Институт физиологически активных веществ
Федерального государственного бюджетного учреждения науки
Федерального исследовательского центра проблем химической физики и медицинской химии
Российской академии наук

Группа синтеза физиологически активных веществ

Области исследований:

q  Синтез и изучение превращений новых высокоэлектрофильных фтор- и хлорсодержащих синтонов, содержащих двухкоординационный азот, в реакциях с нуклеофильными реагентами позволили разработать препаративные методы получения широкого ряда ациклических и гетероциклических соединений: О-замещенных (в том числе фосфорилированных) ацилгидроксимоилхлоридов, циклических фосфоратов, фторсодержащих аминофосфонатов, триазинов, триазинонов, оксадиазинов, диазинов, диазинонов, фторимидазопиридинкарбоксилатов, оксазафосфолинов, 4-амино-5-оксодигидропирролов, имидазооксазолов [1-4].





q  Изучение биологической активности синтезированных веществ показало, что соединения некоторых классов являются перспективными для использования в медицине (обнаружена антимикробная и противоопухолевая активности) и в агрохимии (инсектицидная, фунгицидная, росторегулирующая активности), а также в качестве веществ-анализаторов – ингибиторов протеиназ [5,6].



Биологическая активность некоторых классов синтезированных соединений



q  Разработка методов синтеза разнообразных ациклических и гетероциклических соединений.

Основные результаты:

q  Разработаны препаративные методы получения разнообразных ациклических и гетероциклических соединений: О-замещенных (в том числе фосфорилированных) а цилгидроксимоилхлоридов, циклических фосфоратов, фторсодержащих аминофосфонатов, триазинов, триазинонов, оксадиазинов, диазинов, диазинонов, фторимидазопиридинкарбоксилатов, оксазафосфолинов, 4-амино-5-оксодигидропирролов, имидазооксазолов.

q  Найдены перспективные соединения для использования в медицинской (антимикробная и противоопухолевая активность) и агрохимической (инсектицидная, фунгицидная, росторегулирующая активность) практике и в качестве веществ-анализаторов – ингибиторов протеиназ.

Публикации группы синтеза ФАВ (версия Сhemical Аbstracts)

1. Intramolecular heterocyclization of N-(pyrimidin-2-yl)imines of methyl trifluoropyruvate
   By Sokolov, V. B.; Aksinenko, A. Yu. From Russian Chemical Bulletin (2009), 58(7), 1476-1478. Language: English, Database: CAPLUS
   The reactions of N-(pyrimidin-2-yl)imines of Me trifluoropyruvate with tri-Me phosphite afforded Me 3-fluoroimidazo[1,2-a]pyrimidin-2-carboxylates, which were transformed into N-substituted Me 3-aminoimidazo[1,2-a]pyrimidine-2-carboxylates by the reactions with amines.
   
   
2. Alkyl 2-alkoxy(aryloxy)-2-isocyanato-3,3,3-trifluoropropionates
   By Sokolov, V. B.; Goreva, T. V.; Epishina, T. A.; Aksinenko, A. Yu. From Russian Chemical Bulletin (2009), 58(7), 1533-1537. Language: English, Database: CAPLUS
   Previously unknown fluorinated alkoxy(aryloxy)alkylisocyanates, the esters of alkoxy and aryloxy-2-isocyanato-3,3,3-trifluoropropionic acids, were obtained. The synthetic potential of these compds. were demonstrated in reactions with anilines leading to 2-substituted 3,3,3-trifluoroalanine derivs.
   
   
3. Synthesis of O-phosphorylated 1-substituted 2,2,2-trifluoroethanols, serine hydrolase inhibitors
   By Aksinenko, A. Yu.; Sokolov, V. B.; Goreva, T. V.; Makhaeva, G. F. From Russian Chemical Bulletin (2010), 59(1), 102-106. Language: English, Database: CAPLUS
   Reactivity of trifluoromethyl carbonyl compds. in a two-step reaction with dialkyl phos-phites (the Abramov reaction and phosphonate-phosphate rearrangement) has been studied and the scope of this reaction for the prepn. of O-phosphorylated 1-substituted 2,2,2-trifluoro-ethanols, serine hydrolase inhibitors, has been detd.
   
   
4. Modification of biologically active amides and amines with fluorine-containing heterocycles 2*. N-(2-Thienyl)imines on the base of methyl trifluoropyruvate in cyclocondensation with 1,3-N, N-binucleophiles
   By Sokolov, V. B.; Aksinenko, A. Yu. From Russian Chemical Bulletin (2010), 59(1), 197-199. Language: English, Database: CAPLUS
   An approach to the modification of the biol. active compds., substituted 2-aminothiophenes, with fluorine-contg. five-membered heterocycles is proposed. The reaction of 2-aminothiophenes with Me trifluoropyruvate yields the corresponding N-(2-thienyl)imines, their subsequent cyclocondensation with 1,3-N,N-binucleophiles (2-aminothiazoline and benzamidines) furnished 5-oxo-6-trifluoromethyl-2,3,5,6-tetrahydroimidazothiazoles and 5-oxo-2-phenyl-4-trifluoromethyl-4,5-dihydro-1H-imidazoles.
   
   
5. Modification of biologically active amides and amines with fluorine-containing heterocycles 1. Novel fluorine-containing heterocyclic derivatives of streptocide
   By Sokolov, V. B.; Aksinenko, A. Yu.; Epishina, T. A.; Goreva, T. V.; Martynov, I. V. From Russian Chemical Bulletin (2010), 59(1), 192-196. Language: English, Database: CAPLUS
   An approach to the modification of the known antimicrobial drug, streptocide, with fluorine-contg. five-membered heterocycles is proposed. The reaction of the generated in situ Me 2-[4-(N-acetylamino)phenylsulfonyl]imino-3,3,3-trifluoropropionate with 1,3-C,N- or 1,3-N,N-binucleophiles and subsequent hydrolysis of the resulting products furnished different novel fluorine-contg. heterocyclic derivs. of streptocide, including fused heterocycles.
   
   
6. Modification of biologically active amides and amines with fluorine-containing heterocycles 3*. Piracetam in the three-component reaction with methyl trifluoropyruvate and 1,3-binucleophiles
   By Sokolov, V. B.; Aksinenko, A. Yu.; Epishina, T. A.; Goreva, T. V.; Martynov, I. V. From Russian Chemical Bulletin (2010), 59(1), 288-291. Language: English, Database: CAPLUS
   Three-component reaction of Piracetam, Me trifluoropyruvate and 1,3-binucleophiles, such as 6-aminouracils, 6-aminothiouracils, 4-(4-tolylamino)pent-3-en-2-one and N-substituted ureas, has been studied. This reaction resulted in fluorinated heterocyclic derivs. of Piracetam.
   
   
7. 3-Substituted 2-trifluoromethylimidazo[1,2-a]pyridines
   By Sokolov, V. B.; Aksinenko, A. Yu.; Epishina, T. A.; Goreva, T. V. From Russian Chemical Bulletin (2009), 58(3), 631-633. Language: English, Database: CAPLUS
   3-Fluoro-2-trifluoromethylimidazo[1,2-a]pyridines I (R = 3-Me, 5-Br, etc.) were obtained via the reaction of hexafluoroacetone 2-pyridylimines with tri-Me phosphite. The reaction of I with sodium methoxide gave the corresponding 3-methoxy-2-trifluoromethylimidazo[1,2-a]pyridines.
   
   
8. Reactions of methyl 3,3,3-trifluoro-2-(pyridin-2-ylimino)-propanoates with mono- and difunctional nucleophiles
   By Sokolov, V. B.; Aksinenko, A. Yu. From Russian Journal of General Chemistry (2010), 80(1), 112-116. Language: English, Database: CAPLUS
   Reactions of Me 3,3,3-trifluoro-2-(pyridin-2-ylimino)propanoates with nucleophiles and 1,3-binucleophiles such as methanol, p-toluidine, phenylhydrazine, di-Et phosphonate, 2-amino-2-butenenitrile, benzamidine, and 4,5-dihydro-1,3-thiazol-2-amine gave I (R1 = H, 3-Me, 5-Cl, etc.; R2 = MeO, MeC6H4NH, etc.) and trifluoromethyl-contg. 2-aminopyridines, e.g. II (R3 = H, 4-Me, 5-Me).
   
   
9. Study of the structural determinants of acute and delayed neurotoxicity of O-phosphorylated oximes by molecular field topology analysis (MFTA)
   By Radchenko, E. V.; Makhaeva, G. F.; Sokolov, V. B.; Palyulin, V. A.; Zefirov, N. S. From Doklady Biochemistry and Biophysics (2009), 429, 309-314. Language: English, Database: CAPLUS
   
   
10. Synthesis of 6-substituted 5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidine-2,4-diones and 2-thioxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-ones
    By Aksinenko, A. Yu.; Sokolov, V. B.; Goreva, T. V.; Epishina, T. A.; Pushin, A. N. From Russian Chemical Bulletin (2008), 57(7), 1543-1546. Language: English, Database: CAPLUS
    A three-component reaction of 6-aminouracils and 6-aminothiouracils with formaldehyde and primary amines gave 6-alkyl-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidine-2,4-diones and 6-alkyl-2-thioxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-ones.
    
    
11. Esterase profile and analysis of structure-inhibitor selectivity relationships for homologous phosphorylated 1-hydroperfluoroisopropanols
    By Makhaeva, G. F.; Serebryakova, O. G.; Boltneva, N. P.; Galenko, T. G.; Aksinenko, A. Yu.; Sokolov, V. B.; Martynov, I. V. From Doklady Biochemistry and Biophysics (2008), 423, 352-357. Language: English, Database: CAPLUS
    
    
12. Alkyl 2-chloro-3,3,3-trifluoro-2-isocyanatopropionates
    By Sokolov, V. B.; Goreva, T. V.; Epishina, T. A.; Aksinenko, A. Yu. From Russian Chemical Bulletin (2007), 56(11), 2255-2257. Language: English, Database: CAPLUS
    Two new fluorine-contg. chloroalkylisocyanates, viz., esters of 2-chloro-3,3,3-trifluoro-2-isocyanatopropionic acid, were synthesized starting from urethane and alkyl trifluoropyruvates. The synthetic usefulness of these compds. in the prepn. of 2-substituted derivs. of 3,3,3-trifluoroalanine, and of ethoxycarbonylimine, was demonstrated.
    
    
13. Diethoxyphosphorylimine of methyl trifluoropyruvate in cyclocondensation with 1,3-C,N- and -N,N-binucleophiles
    By Sokolov, V. B.; Aksinenko, A. Yu. From Russian Chemical Bulletin (2007), 56(11), 2252-2254. Language: English, Database: CAPLUS
    Reaction of diethoxyphosphorylimine of Me trifluoropyruvate (MeO2C(CF3)C:NP(O)(OEt)2) with 1,3-C,N- and -N,N-binucleophiles led to a variety of N-phosphorylated fluorine-contg. heterocycles, including the fused ones.
    
    
14. Arenesulfonylimines of methyl trifluoropyruvate in the cyclocondensation reactions with 1,3-C,N- and -N,N-binucleophiles
    By Sokolov, V. B.; Aksinenko, A. Yu.; Martynov, I. V. From Russian Chemical Bulletin (2007), 56(11), 2247-2251. Language: English, Database: CAPLUS
    The cyclocondensation of arenesulfonylimines of Me trifluoropyruvate with 1,3-C,N- and- N,N-binucleophiles led to a variety of N-sulfonylated fluorine-contg. heterocycles, including the fused ones, e.g., I (R1 = H, MeO, Cl, Me; R2 = CH2Ph, 4-ClPh).
    
    
15. Modeling of the relationships between the structure of O-phosphorylated oximes and their anticholinesterase activity and selectivity using molecular field topology analysis (MFTA)
    By Radchenko, E. V.; Makhaeva, G. F.; Malygin, V. V.; Sokolov, V. B.; Palyulin, V. A.; Zefirov, N. S. From . (2007), RU 2305820 C1 20070910. Language: Russian, Database: CAPLUS
    FIELD: heat power engineering.SUBSTANCE: heat exchange plant comprises hollow vertical cylindrical housing connected with the pipeline for supplying fluid and steam, side inlet branch pipe mounted for permitting supply of heated fluid tangentially with respect to the walls of the housing, outlet branch pipe for discharging heated fluid from the housing, and axial inlet branch pipe for supplying steam connected with the steam pipe coaxially mounted inside the housing and having slots provided with tangential deflectors for inflowing steam into the space of the housing. The side inlet branch pipe for supplying heated fluid is mounted in the bottom section of the housing. The outlet branch pipe is mounted in the top section of the housing. The steam pipe is perforated. The face of the pipe is set in the vicinity to the bottom of the housing and its bottom end is plugged. The tangential deflectors are made of a curved plates. The diameter and density of the holes of the perforations of the steam pipe increase toward the bottom section of the pipe. The slots with tangential deflectors are arranged on the steam pipe in rows. The bottom row is mounted on the plugged end of the steam pipe in the zone of supplying of the heated fluid. The plant could be provided with valves mounted in the inlet branch pipes to provide control of the supply of heated fluid and steam.EFFECT: enhanced efficiency.3 cl, 1 dwg.
    
    
16. N-Substituted imines of methyl trifluoropyruvate in the synthesis of 5-amino-5-(trifluoromethyl)hydantoins
    By Aksinenko, A. Yu.; Goreva, T. V.; Epishina, T. A.; Pushin, A. N.; Sokolov, V. B. From Russian Chemical Bulletin (2006), 55(6), 1052-1055. Language: English, Database: CAPLUS
    Cyclocondensation of N-substituted imines of Me trifluoropyruvate with monosubstituted ureas afforded novel 5-amino-5-(trifluoromethyl)hydantoins, e.g., I.
    
    
17. Acylimines of hexafluoroacetone in cyclocondensation with C,N-binucleophiles
    By Sokolov, V. B.; Aksinenko, A. Yu.; Martynov, I. V. From Russian Chemical Bulletin (2006), 55(4), 731-734. Language: English, Database: CAPLUS
    The reactions of acylimines of hexafluoroacetone with 1,3-C,N-binucleophiles giving rise to fluorine-contg. 1,4-dihydropyrimidines, including fused compds., were studied.
    
    
18. Acylimines of methyl trifluoropyruvate in cyclocondensation with C,N-bisnucleophiles
    By Sokolov, V. B.; Aksinenko, A. Yu.; Epishina, T. A.; Goreva, T. V.; Martynov, I. V. From Russian Chemical Bulletin (2005), 54(12), 2851-2856. Language: English, Database: CAPLUS
    Reactions of acylimines of Me trifluoropyruvate with C,N-bisnucleophiles gave fluoro-contg. heterocycles including the 5-oxo-4,5-dihydro-1H-pyrrole fragment.
    
    
19. Intramolecular cyclization of 1-allyl- and 1-methallyl-6-amino-2-thiouracils
    By Sokolov, V. B.; Aksinenko, A. Yu.; Pushin, A. N.; Martynov, I. V. From Russian Chemical Bulletin (2005), 54(7), 1744-1746. Language: English, Database: CAPLUS
    Intramol. cyclization of 1-allyl- and 1-methallyl-6-amino-2-thiouracils afforded 5-amino-2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ones, e.g., I (R = H or Me). Their structures were proved by chem. transformations, spectral and anal. data.
    
    
20. Acylimines of hexafluoroacetone and methyl trifluoropyruvate in cyclocondensation with 2-aminothiazolines
    By Sokolov, V. B.; Aksinenko, A. Yu.; Epishina, T. A.; Goreva, T. V.; Pushin, A. N.; Martynov, I. V. From Russian Chemical Bulletin (2005), 54(7), 1667-1671. Language: English, Database: CAPLUS
    Reactions of acylimines of hexafluoroacetone and Me trifluoropyruvate with 2-aminothiazolines afforded fluorine-contg. heterocycles of two structural types: 6,7-dihydro-2H-thiazolo[3,2-a][1,3,5]triazines, e.g., I (R1 = Me, Cl or F) and 2,3,5,6-tetrahydroimidazo[2,1-b]thiazoles, e.g., II (R2 = H, Me, t-Bu, MeO, Cl or F), resp.
    
    
21. Synthesis of fluoro-containing pyrimidinones from hexafluoroacetone (ethoxycarbonyl)imine
    By Sokolov, V. B.; Aksinenko, A. Yu. From Russian Chemical Bulletin (2005), 54(6), 1518-1522. Language: English, Database: CAPLUS
    Cyclocondensation of hexafluoroacetone (ethoxycarbonyl)imine with various 1,3-C,N-bisnucleophiles afforded novel bis(trifluoromethyl)pyrimidinones, e.g., I and II (R = Me, Ph, p-tolyl, benzyl), in preparative yields.
    
    
22. Acylimines of hexafluoroacetone and methyl trifluoropyruvate in cyclocondensation with 2-aminopyridines
    By Sokolov, V. B.; Aksinenko, A. Yu. From Russian Chemical Bulletin (2005), 54(6), 1514-1517. Language: English, Database: CAPLUS
    Cyclocondensation of acylimines of hexafluoroacetone and Me trifluoropyruvate with 2-aminopyridines afforded earlier unknown fluoro-contg. 2H-pyrido[1,2-a][1,3,5]triazines, e.g., I (X = CF3, COOMe).
    
    
23. Benzamidines in cyclocondensation with hexafluoroacetone and methyl trifluoropyruvate acyl- and ethoxycarbonyl imines
    By Sokolov, V. B.; Aksinenko, A. Yu.; Epishina, T. A.; Goreva, T. V.; Martynov, I. V. From Russian Chemical Bulletin (2005), 54(2), 472-475. Language: English, Database: CAPLUS
    The reactions of hexafluoroacetone and Me trifluoropyruvate acyl- and ethoxycarbonyl imines with benzamidines afford fluoro-contg. heterocycles of four structural types: dihydrotriazines, dihydrotriazinones, imidazoles, and imidazooxazoles.
    
    
24. Reactions of methyl trifluoropyruvate 2-pyridylimines with trimethyl phosphite
    By Sokolov, V. B.; Aksinenko, A. Yu.; Martynov, I. V. From Russian Chemical Bulletin (2005), 54(2), 470-471. Language: English, Database: CAPLUS
    Reactions of Me trifluoropyruvate 2-pyridylimines with tri-Me phosphite afford Me 3-fluoroimidazo[1,2-a]pyridine-2-carboxylates.
    
    
25. Fluorinated aminophosphonates - A new type of irreversible inhibitors of serine hydrolases
    By Makhaeva, G. F.; Malygin, V. V.; Aksinenko, A. Yu.; Sokolov, V. B.; Strakhova, N. N.; Rasdolsky, A. N.; Richardson, R. J.; Martynov, I. V. From Doklady Biochemistry and Biophysics (2005), 400, 92-95. Language: English, Database: CAPLUS
    
    
26. Fluorinated triazinones from hexafluoroacetone ethoxycarbonylimine
    By Sokolov, V. B.; Aksinenko, A. Yu. From Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya) (2003), 52(10), 2167-2170. Language: English, Database: CAPLUS
    The behavior of hexafluoroacetone ethoxycarbonylimine in cyclocondensation with various binucleophiles of the amidine type, viz., amino derivs. of N- and N,S-heterocycles, was studied. A preparative method for the synthesis of previously unknown annelated 2,2-bis(trifluoromethyl)-1,3,5-triazinones was developed.
    
    
27. A convenient synthesis of 3,3,3-trifluoroalanine derivatives
    By Aksinenko, A. Yu.; Pushin, A. N.; Sokolov, V. B. From Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya) (2002), 51(11), 2136-2138. Language: English, Database: CAPLUS
    A one-pot synthesis of N-substituted 3,3,3-trifluoroalanine esters from alkyl trifluoropyruvates and carboxamides or substituted ureas was developed. Reaction of F3CC(O)C(O)OR (R = Me, Et) with R1C(O)NH2 (R1 = OEt, Me-3-C6H4, Me -4-C6H4, F-4-C6H4-, Me, Et, CH2Cl, Ph, MeNH, AcNH, or PhNH) gave, through a series of intermediates, title products R1C(O)NHCH(CF3)C(O)OR in yields ranging from 57-85%.
    
    
28. Reaction of 6-amino-1,3-dimethyluracil with hexafluoroacetone and ethyl trifluoropyruvate benzoylimines
    By Sokolov, V. B.; Aksinenko, A. Yu.; Martynov, I. V. From Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya) (2001), 50(6), 1113-1114. Language: English, Database: CAPLUS
    Heating of 6-amino-1,3-dimethyluracil with hexafluoroacetone and Et trifluoropyruvate benzoylimines in DMF in the presence of Et3N results in 1,3-dimethyl-7-phenyl-5,5-bis(trifluoromethyl)-1,2,3,4,5,8-hexahydropyrimido[4,5-d]pyrimidine-2,4-dione and 5-benzoylamido-1,3-dimethyl-5-trifluoromethyl-1,2,3,4,5,6-hexahydropyrrolo[2,3-d]pyrimidine-2,4,6-trione, resp.
    
    
29. Fluorinated 1-methylaminoalkylphosphonates. Interaction with ammonia and methylamine
    By Levkovskii, A. V.; Aksinenko, A. Yu.; Pushin, A. N.; Sokolov, V. B. From Phosphorus, Sulfur and Silicon and the Related Elements (1999), 144-146, 827-828. Language: English, Database: CAPLUS
    
    
30. Fluorinated 1,4,2-oxazaphospholines and their opening by nucleophiles
    By Aksinenko, A. Yu.; Sokolov, V. B. From Phosphorus, Sulfur and Silicon and the Related Elements (1999), 144-146, 825. Language: English, Database: CAPLUS
    
    
31. A new inhibitor of pyrimidine phosphorylases
    By Dmitrieva, N. A.; Molchan, O. K.; Komissarov, A. A.; Sokolov, V. B.; Aksinenko, A. Yu.; Pushin, A. N.; Chekhlov, A. N.; Debabov, V. G. From Bioorganicheskaya Khimiya (1998), 24(12), 920-925. Language: Russian, Database: CAPLUS
    5,5-Bis(hydroxymethyl)-2-oxo-[1-(2-trifluoromethyl)-3,3,3-trifluoropropionamido]-1-trifluoromethyl-2.2,2-trifluoroethyl-1,3,2-dioxaphosphan (CA-423) is an in vitro inhibitor of the Escherichia coli uridine and thymidine phosphorylases. Unlike widely studied nucleoside analogs, this compd. binds to the enzymes irreversibly. Its LD50 in mice was 40 mg/kg. Due to the involvement of pyrimidine phosphorylases in carcinogenesis and the relatively low toxicity of CA-423, it is promising for anticancer therapy.
    
    
32. Convenient method for the synthesis and some transformations of the lithium salt of bis(diethoxyphosphoryl)fluoromethane
    By Martynov, B. I.; Sokolov, V. B.; Aksinenko, A. Yu.; Goreva, T. V.; Epishina, T. A.; Pushin, A. N. From Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya) (1998), 47(10), 1983-1984. Language: English, Database: CAPLUS
    A convenient method was developed for the synthesis of the Li salt of 1,1-bis(diethoxyphosphoryl)fluoromethane from available O,O-di-Et (chlorofluoromethyl)phosphonate, and some transformations of the resulting salt were studied.
    
    
33. Cyclization of N-allylthiourea derivatives by the action of chloronitroso alkanes
    By Tkachenko, S. E.; Pushin, A. N.; Sokolov, V. B.; Fedoseev, V. M.; Martynov, I. V. From Chemistry of Heterocyclic Compounds (New York)(Translation of Khimiya Geterotsiklicheskikh Soedinenii) (1998), 34(3), 347-350. Language: English, Database: CAPLUS
    The difficultly available 2-amino-5-chloromethyl-2-thiazolines I (R, R1 = H, H; H, Ph; Et, Et) were prepd. by cyclization of N-allylthioureas H2C:CHCH2NHC(:S)NRR1 via treatment with chloronitroso alkanes, e.g., ClCMe2NO. The reaction proceeds as a halogenophilic process leading to intermediate formamidinesulfenyl chloride which is rapidly and selectively cyclized to give 2-amino-2-thiazolines.
    
    
34. Hexafluoroacetone dialkoxyphosphorylimines
    By Korenchenko, O. V.; Aksinenko, A. Yu.; Sokolov, V. B.; Pushin, A. N. From Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya) (1998), 47(7), 1369-1373. Language: English, Database: CAPLUS
    Reactions of hexafluoroacetone dialkoxyphosphorylimines with NH-, PH-, and CH- nucleophiles, tri-Me phosphite, and N,N-dimethylaniline, and the [2+4]-cycloaddn. reaction were studied.
    
    
35. Reaction of N-cyanoamines with polyfluorocarbonyl compounds
    By Sokolov, V. B.; Aksinenko, A. Yu. From Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya) (1998), 47(4), 727-728. Language: English, Database: CAPLUS
    N-cyanoamines RCN (R = Me2N, morpholino) reacted with CF3COX (X = COOEt, CF3) in anhyd. ether at -200C for 24 h to give I in around 89% yields.
    
    
36. Crystal and molecular structures and synthesis of O,O-diisopentyl 1-(phenylsulfonamido)-1-(trifluoromethyl)-2,2,2-trifluoroethylphosphonate
    By Chekhlov, A. N.; Aksinenko, A. Yu.; Sokolov, V. B.; Martynov, I. V. From Doklady Akademii Nauk (1995), 345(3), 360-363. Language: Russian, Database: CAPLUS
    Reaction of (CF3)2C:NSO2Ph and (Me2CHCH2CH2O)2P(O)H in Et2O gave 85% title compd. (Me2CHCH2CH2O)2P(O)C(CF3)2NHSO2Ph, the structure of which was detd. by x-ray crystallog.
    
    
37. (Alkoxycarbonyl)imines of hexafluoroacetone in [2 + 4]-cycloaddition
    By Korenchenko, O. V.; Aksinenko, A. Yu.; Sokolov, V. B.; Pushin, A. N.; Martynov, I. V. From Izvestiya Akademii Nauk, Seriya Khimicheskaya (1995), (9), 1809-13. Language: Russian, Database: CAPLUS
    The [2 + 4]-cycloaddns. of hexafluoroacetone (alkoxycarbonyl)imines to 1,3-cyclopentadiene (I), cyanoguanidines (II), and cyanamides (III) were examd. The reactions with I gave azanorbornenes; reactions with II and III gave oxadiazines, e.g., IV.
    
    
38. Unusually strong intramolecular C-H...N hydrogen bond in 3-(hydroperfluoroisobutyryl)-2-[(hydroperfluoroisobutyryl)imino]-1,3-thiazolidine
    By Chekhlov, A. N.; Aksinenko, A. Yu.; Pushin, A. N.; Sokolov, V. B. From Izvestiya Akademii Nauk, Seriya Khimicheskaya (1995), (8), 1593-5. Language: Russian, Database: CAPLUS
    X-ray anal. of the title compd. (I) revealed an unusually strong intramol. C-H...N hydrogen bond with the shortest H...N distance reported so far, 2.00(3) A.
    
    
39. Synthesis and x-ray structural study of 4-oxo-2,2-bis(trifluoromethyl)-2,3,4-trihydro-9-thia-1,3,4a-triazafluorene
    By Chekhlov, A. N.; Korenchenko, O. V.; Aksinenko, A. Yu.; Sokolov, V. B.; Martynov, I. V. From Doklady Akademii Nauk (1994), 339(4), 503-6. Language: Russian, Database: CAPLUS
    The title compd. (I) was prepd. from 2-benzothiazolamine and (CF3)2C:NCOOEt. X-ray anal. of I showed that the triazinone ring has a compressed, distorted boat conformation and the 5-membered ring has a strongly compressed envelope conformation.
    
    
40. Crystal and molecular structure and synthesis of 4-oxo-2,2-bis(trifluoromethyl)-3-(ethoxycarbonyl)-1,2,3,4-tetrahydroquinazoline
    By Chekhlov, A. N.; Korenchenko, O. V.; Aksinenko, A. Yu.; Sokolov, V. B.; Martynov, I. V. From Doklady Akademii Nauk (1994), 339(6), 776-81. Language: Russian, Database: CAPLUS
    The title compd. (I) was prepd. from anthranilic acid and (CF3)2C:NCOOEt. X-ray anal. of I indicated that the heterocyclic ring exists in a distorted half-boat conformation.
    
    
41. 2-Alkoxyhexafluoro-2-propyl isocyanates
    By Korenchenko, O. V.; Aksinenko, A. Yu.; Sokolov, V. B.; Pushin, A. N. From Izvestiya Akademii Nauk, Seriya Khimicheskaya (1995), (2), 390-2. Language: Russian, Database: CAPLUS
    The title compds. were prepd. by treatment of (CF3)2C(OR)NHCOOEt (R = Me, Et) with PCl5. Reactions of the isocyanates with amines and alcs. were studied.
    
    
42. Synthesis and structure of 5-amino(diethylamino)methyleneamino-3,3,4-trimethyl-2-oxo-2-ethoxy-?5-1,4,2-diazaphospholine
    By Chekhlov, A. N.; Levkovskii, A. V.; Sokolov, V. B.; Aksinenko, A. Yu.; Martynov, I. V. From Doklady Akademii Nauk (1994), 334(2), 200-3. Language: Russian, Database: CAPLUS
    Heating cyaniminodiazaphospholidine I in Et2NH gave 49% title compd. II, the structure of which was detd. by x-ray crystallog.
    
    
43. The easy P-C-bond cleavage of fluorinated phosphine oxide
    By Aksinenko, A. Yu.; Pushin, A. N.; Sokolov, V. B. From Phosphorus, Sulfur and Silicon and the Related Elements (1993), 84(1-4), 249-51. Language: English, Database: CAPLUS
    Treatment of (1-acetamido-1-trifluoromethyl-2,2,2-trifluoroethyl)diphenyl phosphine oxide by OH-nucleophiles leads to the P-C(sp3) bond cleavage. Thus, hydrolysis or methanolysis of Ph2P(O)C(CF3)2NHCOMe gave Ph2P(O)OH and Ph2P(O)OMe resp.
    
    
44. Preparation and crystal structure of the monohydrate of the zwitterion of 3,3,4-trimethyl-5-[bis(dimethylamino)methyleneamino]-2-hydroxy-2-oxo-?5-1,4,2-diazaphospholine By Chekhlov, A. N.; Levkovskii, A. V.; Aksinenko, A. Yu.; Sokolov, V. B.; Martynov, I. V. From Doklady Akademii Nauk (1993), 332(3), 338-41. Language: Russian, Database: CAPLUS Treating (EtO)2P(O)CMe2NMeCF:NCF3 with 1:1 NH3 and Me2NH in EtOH gave 10% title zwitterion I, the structure of which was detd. by x-ray crystallog.
45. Synthesis of phosphorylated alkylchloroformoximes
    By Lyashenko, Yu. E.; Sokolov, V. B. From Phosphorus, Sulfur and Silicon and the Related Elements (1993), 78(1-4), 153-9. Language: English, Database: CAPLUS
    Various phosphorylated alkylchloroformoximes, e.g., R'OP(O)XON:CMeCl (R' = alkyl, X = alkylthio, PhO, EtOCH2CH2O, HCF2CF2CH2O, Et2N, morpholino, alkoxy), contg. a -O-N:C(Alk)Cl group (hydroxamic acids chlorides) can be obtained in a one-pot synthesis with yields up to 73% from alcs., dichloronitrosoalkanes and corresponding phosphorus(III) dichlorides. Thus, addn. of (HCF2CF2CH2O)PCl2 to a mixt. of MeCCl2NO and 2 equiv Me2CHOH at -10°, then for 2 h at room temp. afforded HCF2CF2CH2OP(O)(OCHMe2)ON:CMeCl (E and Z isomers) in 73% yield. Reactions proceed through the corresponding diesters and esters of phosphorus(III).
    
    
46. Molecular refraction of nitroso compounds
    By Martynov, I. V.; Sokolov, V. B.; Ivanov, A. N. From Doklady Akademii Nauk (1993), 333(2), 193-6. Language: Russian, Database: CAPLUS
    A review with 14 refs. is presented, based on literature data as well as that obtained by the authors, on the refraction of both C- and N-nitroso compds. and a comparative anal. of the dependence of the MR (mol. refraction) of nitro- and nitroso-alkanes on their structures.
    
    
47. Paradoxical toxic effect and calcium antagonism of the cholinesterase inhibitors O-(N-arylcarbamoyl)acylhydroximoyl chlorides
    By Ivanov, Yu. Ya.; Sokolov, V. B.; Epishina, T. A.; Martynov, I. V. From Doklady Akademii Nauk (1993), 328(6), 744-6 [Biochem.]. Language: Russian, Database: CAPLUS
    N-phenylcarbamates and aliph. analogs of the formula R R1N(O)ON::C(Cl)R2 [where R = Et, Me, and Ph; R1 = H, Me; R2 = Et, Pr, iso-Pr] were examd. for their acetylcholinesterase and butyrylcholinesterase inhibition, for their acute toxicity and their action on selective organs. The enzyme inhibition depended on their mol. structure. Paradoxical effects (higher dose and low toxicity and vice versa) were noted.
    
    
48. Synthesis and structure of O-(arylcarbamoyl)butyrohydroximoyl chlorides
    By Sokolov, V. B.; Chekhlov, A. N.; Epishina, T. A.; Martynov, I. V. From Izvestiya Akademi Nauk, Seriya Khimicheskaya (1992), (2), 315-19. Language: Russian, Database: CAPLUS
    The title compds. I (R = H, o-, m-, p-Me, p-Br, 3,4-Cl2) were prepd. in 43.7-79.1% yields from ClCO2N:CClPr and RC6H4NH2 and the crystal and mol. structure of I (R = m-Me) was detd. by x-ray anal. The x-ray data also confirmed that all the prepd. compds. were Z-isomers.
    
    
49. Synthesis of fluorinated 2-oxo-1,4,2-oxazaphosphol-4-ines and their opening by alcohols
    By Korenchenko, O. V.; Aksinenko, A. Yu.; Sokolov, V. B.; Martynov, I. V. From Heteroatom Chemistry (1992), 3(2), 147-50. Language: English, Database: CAPLUS
    Trifluoromethyl-substituted 1,4,2?5-oxazaphosphol-4-ines from phosphorus dichlorides and N-acylimines of hexafluoroacetone were synthesized and characterized by 1H, 19F, and 31P NMR. Alcs. open these oxazaphospholines at the P-O bond, forming the corresponding esters.
    
    
50. Synthesis and anticholinesterase activity of fluorine-containing aminophosphoryl compounds
    By Korenchenko, O. V.; Ivanov, Yu. Ya.; Aksinenko, A. Yu.; Sokolov, V. B.; Martynov, I. V. From Khimiko-Farmatsevticheskii Zhurnal (1992), 26(6), 21-3. Language: Russian, Database: CAPLUS
    Reaction of R2P(O)H (R = MeO, EtO, PrO, Me2CHO, Ph) with (CF3)2C:NCOR1 (R1 = OEt, OCH2Ph, OPr, OBu, OCH2CH2CHMe2, CF3) in Et2O gave 44-93% R2P(O)C(CF3)2NHCOR1. Treating a 1,4,2-oxazaphospholine deriv. with alcs. gave Me(R)P(O)C(CF3)2NHCO2Et (R = BuO, Me2CHO). Bimol. rate consts. for inhibition of cholinesterases by these compds. were detd.
    
    
51. Anticholinesterase activity of O-carbamoylated acylhydroxymoyl chlorides
    By Ivanov, Yu. Ya.; Epishina, T. A.; Sokolov, V. B. From Khimiko-Farmatsevticheskii Zhurnal (1992), 26(5), 62-3. Language: Russian, Database: CAPLUS
    A series of O-carbamoyl acylhydroxymoyl chloride compds. RR1NCO2N:CClR2 [R = (un)substituted Ph; R1 = H, Me; R2 = alkyl] have been synthesized and their interaction with human erythrocyte acetylcholinesterase and equine serum butyrylcholinesterase was studied. The biomol. inhibition rate consts. for irreversible acetylcholinesterase and butyrylcholinesterase were found to range from 2.4 ? 104 to 8.9 ? 106M-1 min-1.
    
    
52. Reactions of O-(alkylchloroformoimino)trichloromethylphosphoranes with S-nucleophiles
    By Lyashenko, Yu. E.; Sokolov, V. B. From Phosphorus, Sulfur and Silicon and the Related Elements (1992), 69(1-2), 153-61. Language: English, Database: CAPLUS
    Interactions of O-(alkylchloroformoimino)trichloromethylphosphoranes MePCl3ON:CR'Cl (I; R' = Me, Et, Pr, CHMe2, Bu, CH2Cl) with hydrogen sulfide and mercaptans are reported; interaction of I (R' = Me) with 2-mercaptoethanol to give MeP(O)ClON:CMeSCH2CH2Cl is discussed and activation of the chlorine at an sp2 hybridized carbon by means of the phosphorane fragment is demonstrated in the substitution reactions with S-nucleophiles; the method of P:S bond formation in chlorophosphoranes by means of the reaction with thioacetic acid is suggested; some derivs. of O-alkylchloroformooximes are described.
    
    
53. Inhibition of enzymic activity of thrombin by a low molecular weight synthetic inhibitor
    By Kireeva, E. G.; Strukova, S. M.; Dugina, T. N.; Sokolov, V. B.; Aksinenko, A. Yu. From Biokhimiya (Moscow) (1992), 57(1), 21-6. Language: Russian, Database: CAPLUS
    The effect of the organophosphoric inhibitor, SA-152, on the fibrinogen-coagulating and TAME-esterase activity of bovine thrombin was studied. The irreversible inhibition consts. (kII = 1.1 ? 104 M-1•min-1, Ki = 0.7 ? 10-4M, k2 = 0.8 min-1 towards the coagulating activity and kII = 0.7 ? 104 M-1•min-1, Ki = 0.3 ? 10-4M, k2 = 0.2 min-1 towards the esterase activity) were detd. The SA-152 inactivated thrombin was dialyzed and incubated with 0.5M and 2.5M NaCl and 10 mM TAME. There was no reconstitution of activity of the SA-152 modified thrombin after dialysis and treatment with high concns. of NaCl and TAME. Heparin interactions with the anion-binding site of the high mol. wt. recognition center in the thrombin mol. did not significantly influence the values of the kinetic consts. for the enzyme inhibition by SA-152. This finding is consistent with the hypothesis on the irreversible binding of SA-152 in the active center of the enzyme.
    
    
54. Sterically strained molecular structure of (1-acetamido-1-trifluoromethyl-2,2,2-trifluoroethyl)diphenylphosphine oxide
    By Chekhlov, A. N.; Aksinenko, A. Yu.; Sokolov, V. B.; Martynov, I. V. From Doklady Akademii Nauk SSSR (1991), 319(6), 1396-400 [Phys. Chem.]. Language: Russian, Database: CAPLUS
    The crystal and mol. structure of Ph2P(O)C(CF3)2NHCOMe was detd. by x-ray crystallog.
    
    
55. Reaction of (chloroformyl)alkanohydroximoyl chlorides with triphenylphosphine in the presence of trimethylsilyl azide
    By Sokolov, V. B.; Epishina, T. A.; Ivanov, A. N.; Martynov, I. V. From Zhurnal Obshchei Khimii (1991), 61(5), 1268-9. Language: Russian, Database: CAPLUS
    Reaction of ClCO2N:CRCl (R = Me, Et, Pr) with Ph3P and Me3SiN3 gave Ph3P:NCO2N:CRCl in ?73% yield.
    
    
56. Reaction of (O-triphenylphosphiminoformyl)isobutyrohydroxymoyl chloride with hexafluoroacetone
    By Sokolov, V. B.; Epishina, T. A.; Korenchenko, O. V.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1991), (8), 1921-3. Language: Russian, Database: CAPLUS
    Reaction of Ph3P:NCO2N:CClCHMe2 with (CF3)2CO in Et2O gave 69.1% (CF3)2C(N:CO)ON:CClCHMe2 (I) via sigmatropic rearrangement of initially formed (CF3)2C:NCO2N:CClCHMe2. The structure of I was confirmed by IR and NMR spectroscopy and by its reactions with Ph2P(O)H and 3,4-dichloroaniline.
    
    
57. Crystal and molecular structure of the acetonitrile semisolvate monohydrate of the 2-hydroxy-2-oxo-1,3,3,4-tetramethyl-5-(N,N'-dimethylamidinoformyl)imino-1,4,2-diazaphospholan zwitterion
    By Chekhlov, A. N.; Levkovskii, A. V.; Aksinenko, A. Yu.; Sokolov, V. B.; Martynov, I. V. From Doklady Akademii Nauk SSSR (1991), 317(6), 1413-17 [Phys. Chem.]. Language: Russian, Database: CAPLUS
    The title compd. is monoclinic, space group P21/n, with a 8.962(3), b 17.779(3), c 9.816(3) A, and ? 96.84(2)°; dc = 1.85 for Z = 4. The at. parameters are given. The structure was solved by direct methods and refined by least-squares to R = 0.035. The bond lengths and angles are given and the H-bonding is described.
    
    
58. O-Alkyl O-methylchloroformimino phenylphosphonates - effective inhibitors of the hen brain neurotoxic esterase
    By Makhaeva, G. F.; Kononova, I. V.; Malygin, V. V.; Lyashenko, Yu. E.; Sokolov, V. B.; Martynov, I. V. From Doklady Akademii Nauk SSSR (1991), 317(4), 1009-12 [Biochem.]. Language: Russian, Database: CAPLUS
    The title phosphonates were effective inhibitors of neurotoxic esterase; with increasing hydrophobicity the compds. showed pronounced and selective biol. activity towards brain neurotoxic esterase compared to acetylcholinesterase. Thus, the structure of phenylphosphonate played a major role in the inhibitory effects of these potential pesticides towards neurotoxic esterase or acetylcholinesterase.
    
    
59. Conversions of the adducts of dichloronitrosoalkanes with dichlorophosphines
    By Lyashenko, Yu. E.; Sokolov, V. B.; Martynov, I. V. From Phosphorus, Sulfur and Silicon and the Related Elements (1991), 60(1-2), 85-95. Language: English, Database: CAPLUS
    Reaction of RPCl2 (R = Me, Ph, BrCH2, etc.) with R1CCl2NO (R1 = Me, Pr, etc.) in an inert solvent gave adducts RPCl3ON:CClR1 (I). I showed high hygroscopicity and underwent slow decompn. even under moisture-free conditions. Treating I (R = Ph) with SO2 at 0 to +5° gave PhP(O)Cl2. However, treating I (R = Ph, Me, CH2Br, etc.) with SO2 at -12° gave RP(O)ClON:CClR1. Treating I with alcs. R2OH (R2 = alkyl) gave RP(O)(OR2)ON:CClR1.
    
    
60. Synthesis and anticholinesterase activity of O-carbamoylated alkylchloroform oximes
    By Sokolov, V. B.; Ivanov, Yu. Ya.; Epishina, T. A.; Martynov, I. V. From Khimiko-Farmatsevticheskii Zhurnal (1991), 25(4), 33-4. Language: Russian, Database: CAPLUS
    Treating ClCO2N:CClR (R = Me, Et, Pr, CHMe2) with NHR1R2 (R1 = R2 = H, Me, Et; R1 = H, R2 = Me) in Et2O gave 50-69% R1R2NCO2N:CClR (same R-R3), which are acetyl- and butyrylcholinesterase inhibitors (k11 = 1.1 ? 10-2 to 5.4 ? 10-6 M-1 min-1). Acute oral toxicity in mice ranged from 32 to 565 mg/kg.
    
    
61. Influence of 4-ethyl-bicyclic phosphate esters (4-E-BPE) on evoked potentials in hippocampal slices
    By Pervukhin, G. Ya.; Sharonova, I. N.; Prokof'ev, S. E.; Fedorov, N. B.; Sokolov, V. B.; Martynov, I. V. From Byulleten Eksperimental'noi Biologii i Meditsiny (1991), (4), 339-41. Language: Russian, Database: CAPLUS
    Influence of 4-ethyl-bicyclic phosphate ester (4-E-BPE) on the amplitude of population spikes (PS) evoked in CA1 area by Shaffer collateral stimulation in hippocampal slices were analyzed. Bath application of 4-E-BPE (10-6 ? 10-5M) led to a pronounced increase in the amplitude of the PS, the appearance of secondary PS and then introduction of GABA led to restoring original state. The 4-E-BPE was more potent than picrotoxin. These findings suggest that 4-E-BPE suppresses inhibitory synaptic transmission in the CA1 region of hippocampus.
    
    
62. Reaction of fluorine-containing 1,4,2-oxazaphospholine with OH-nucleophiles
    By Korenchenko, O. V.; Aksinenko, A. Yu.; Sokolov, V. B.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1991), (1), 239-40. Language: Russian, Database: CAPLUS
    Treating oxazaphospholine I with ROH (R = H, Me, Et, Pr, Bu, n-pentyl, n-hexyl) in Et2O gave 50-100% ROP(O)MeC(CF3)2NHCO2Et.
    
    
63. Reaction of hexafluoroacetone ethoxycarbonylimine with trimethyl phosphite
    By Korenchenko, O. V.; Aksinenko, A. Yu.; Sokolov, V. B.; Pushin, A. N.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1990), (12), 2879-50. Language: Russian, Database: CAPLUS
    (CF3)2C:NCO2Et reacted with (MeO)3P in CH2Cl2 at 0° to give 49.6% CF2:C(CF3)NMeCO2Et, which reacted with (Me3Si)2NH in Et2O at 100° to give 54.8% CF3CH(CN)NMeCO2Et.
    
    
64. Inhibition of cholinesterase activity by fluorine-containing derivatives of aminoalkylphosphonic acids
    By Kuusk, V. V.; Morozova, I. V.; Agabekyan, R. S.; Aksinenko, A. Yu.; Epishina, T. A.; Sokolov, V. B.; Kovaleva, N. V.; Razdol'skii, A. N.; Fetisov, V. I.; Martynov, I. V. From Bioorganicheskaya Khimiya (1990), 16(11), 1500-8. Language: Russian, Database: CAPLUS
    A series of O,O-diethyl-1-(N-hydrohexafluoroisobutyryl)aminoalkylphosphonates (APh) has been synthesized and their interaction with human erythrocyte acetylcholinesterase (AChE) and with horse serum butyrylcholinesterase (BuChE) studied. Most of the APhs inactivated the cholinesterases irreversible through formation of the enzyme-inhibitor intermediate. The inactivation rate consts. and the enzyme-inhibitor intermediate dissocn. consts. are calcd. The quant. structure-activity relationships including both hydrophobic and calcd. steric parameters of substituents are developed for APh-ChE interactions. Mol. mechanics (program MM2) was used for detg. steric parameters (Es). On the basis of QSAR models anal. it was concluded that hydrophobic interactions play an essential role in APh-AChE binding, whereas for APh-BuChE binding steric interactions are essential. Presence of at least two APh binding centers on the surface of AChE and BuChE is suggested.
    
    
65. The effects of bicyclic phosphoric acid esters and picrotoxin on gamma-aminobutyric acid binding in the GABA-A receptor ionophore complex
    By Pervukhin, G. Ya.; Maslov, A. A.; Sokolov, V. B.; Fetisov, V. I.; Martynov, I. V. From Neirokhimiya (1989), 8(3), 400-4. Language: Russian, Database: CAPLUS
    Individual components of the GABA-A receptor are capable of mutual allosteric interactions. Allosteric interactions between the specific binding sites in the GABA-dependent receptor-channel complex were investigated in rat brain synaptosome and membrane prepns. Paired competitive comparisons for bicyclic phosphorus esters (PBE), picrotoxin, and [3H]GABA were performed. The effects of BPE and picrotoxin on the GABA-dependent permeability for 36Cl- in vitro were also examd. With the combined use of picrotoxin and 4-Me, 4-Et, and 4-Pr derivs. of BPE, the inhibitory effects of picrotoxin in [3H]GABA binding were diminished. Differences in the effect of BPE and picrotoxin on the transport of 36Cl- into synaptoneurosomes were also found. The results are discussed in terms of possible allosteric interactions between the binding sites for BPE, picrotoxin, and [3H]GABA.
    
    
66. Reaction of the adduct of methyldichlorophosphine and 1,1-dichloro-1-nitrosoethane with thioacetic acid
    By Lyashenko, Yu. E.; Sokolov, V. B.; Martynov, I. V. From Zhurnal Obshchei Khimii (1990), 60(8), 1923-4. Language: Russian, Database: CAPLUS
    Treating MePCl2 with MeCCl2NO in PhMe, followed by addn of 1 or 2 equiv AcSH gave 56% MeP(S)ClON:CMeCl or 32% MeP(S)ClON:CMeSAc, resp.
    
    
67. Synthesis and structure of 2-ethoxy-2-oxo-3,3,4-trimethyl-5-[2-ethoxy-4H-4,4-bis(trifluoromethyl)-1,3,5-oxadiazin-6-yl]imino-1,4,2-diazaphospholane
    By Chekhlov, A. N.; Aksinenko, A. Yu.; Korenchenko, O. V.; Sokolov, V. B.; Fokin, E. A.; Martynov, I. V. From Zhurnal Obshchei Khimii (1990), 60(8), 1739-45. Language: Russian, Database: CAPLUS
    Treating oxodiazaphospholane I with (CF3)2C:NCO2Et in Et2O gave 92% title compd. II, the structure of which was detd. by x-ray crystallog.
    
    
68. Analysis of vibrational spectra of normal and deuterated hexafluoroacetonimine
    By Trepalin, S. V.; Aksinenko, A. Yu.; Sokolov, V. B. From Zhurnal Fizicheskoi Khimii (1990), 64(8), 2045-9. Language: Russian, Database: CAPLUS
    The vibrational spectra were studied of hexafluoroacetonimine [(CF3)2CNH]. By using isotope substitution (H/D), the earlier calcd vibrational attributes were more precisely defined. The vibrational spectra of (CF3)2CNH are described by the C5-symmetry model. The inverse vibrational problem was solved in an approxn. of the valence-force field. The IR spectra of gaseous and solid samples and the Raman spectra of all the aggregate states were studied. The IR spectra were recorded on a Fourier spectrometer with a resoln. of 0.5 cm-1 in the 100-4000 cm-1 range. The IR spectra with high resoln. (0.1 cm-1) were recorded at 30-350 cm-1 using a Ge bolometer cooled with liq. He. The Raman spectra were obtained with a resoln. of 3 cm-1 (50-4000 cm-1). The obtained valence-force field can be used for anal. of the vibrational spectra of other N-substituted hexafluoroacetonimines.
    
    
69. Phosphorus-containing N'-(trifluoromethyl)carbodiimides and N'-(trifluoromethyl)fluoroformamidines in reactions with nucleophilic reagents
    By Martynov, I. V.; Aksinenko, A. Yu.; Sokolov, V. B.; Chekhlov, A. N.; Pushin, A. N.; Korenchenko, O. V. From Phosphorus, Sulfur and Silicon and the Related Elements (1990), 49-50(1-4), 223-6. Language: English, Database: CAPLUS
    A review contg. 12 refs.
    
    
70. Interaction of O-phosphorylated oximes with esterases in warm-blooded animals. Role of esterases in toxicity
    By Makhaeva, G. F.; Yankovskaya, V. L.; Kochetova, L. M.; Beznosko, B. K.; Sokolov, V. B.; Brel, V. K.; Malygin, V. V.; Martynov, I. V. From Fiziologicheski Aktivnye Veshchestva (1989), 21, 68-74. Language: Russian, Database: CAPLUS
    Inhibition consts. kII [M-1 min-1] of 42 O-phosphorylated oximes (potential pesticides) for acetylcholinesterase, butyrylcholinesterase, and carboxylesterase and equations for antiesterase activity dependence on hydrophobicity of several of the oximes are presented. The effects of substituents on antiesterase and hydrophobic activities are discussed. Recovery rates of the esterase activities in blood and liver of mice after systemic administration of some of the oximes are also described.
    
    
71. O-(alkylchloroformimino)-O-alkylphosphoric acid chlorides
    By Sokolov, V. B.; Ivanov, A. N.; Goreva, T. V.; Epishina, T. A.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1990), (5), 1122-5. Language: Russian, Database: CAPLUS
    Reaction of (ON)CCl2R with (R'O)2PCl (R, R' = alkyl) afforded the title compds. (R'O)ClP(O)ON:CRCl (I) in up to 69% yield. Hydrolysis of I led to substitution of P-, and not C-bound Cl, resulting in (R'O)(NH4O)P(O)ON:CRCl.
    
    
72. Interaction of 1,1-dichloro-1-nitrosoalkanes with carboxylic acid chlorides and zinc
    By Epishina, T. A.; Sokolov, V. B.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1990), (2), 477-8. Language: Russian, Database: CAPLUS
    R1CON:CRCl (R = Me, Et, R1 = Me; R = Et, R1 = Pr, Me2CH; R = Pr, R1 = Me2CH; R = CH2Cl, R1 = Pr, Me2CH) were prepd. in 11.8-46.8% yields by treating RC(NO)Cl2 with R1COCl in Et2O-contg. Zn 2 h at ambient temp.
    
    
73. An analysis of vibrational spectra of (CF3)2CFNCO and (CF3)2CClNCO
    By Trepalin, S. V.; Aksinenko, A. Yu.; Korenchenko, O. V.; Sokolov, V. B. From Zhurnal Prikladnoi Spektroskopii (1990), 52(5), 813-18. Language: Russian, Database: CAPLUS
    Vibrational spectra (30-4000 cm-1) of (CF3)2CFNCO and (CF3)2CClNCO were investigated. The dihedral angle F(CL)-C-N:C of the only stable conformer is equal to 0°. On the basis of polarized measurements in the Raman spectra, the calcn. of transition intensities in IR spectra by the MNDO method and of application of the data on relative compds., the assignment of vibrations was carried out and inverse vibrational problem was solved.
    
    
74. Electron-donating and -accepting functions of physiologically active and model compounds. XV. Use of the multiplicative factor rule for estimation of the thermodynamic characteristics of hydrogen bonds of difluoronitroacetanilides with phosphonylated oximes
    By Grigor'ev, V. Yu.; Solov'ev, V. P.; Raevskii, O. A.; Ivanov, A. N.; Sokolov, V. B.; Martynov, I. V. From Zhurnal Obshchei Khimii (1990), 60(3), 527-30. Language: Russian, Database: CAPLUS
    The multiplicative method was used to calc. the thermodn. parameters for H bonding between RC6H4NHCOCF2NO2 (R = 3-F, 4-Me, 4-O2N) or PhOH and BuOP(O)MeON:CClR1 (R1 = Me, Et, Pr) or HMPTA or Et2O.
    
    
75. Interaction of 1,1-dichloro-1-nitrosoalkanes with S-ethylmethylphosphonous chloride in the presence of sulfur dioxide
    By Sokolov, V. B.; Ivanov, A. N.; Epishina, T. A.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1990), (2), 464-5. Language: Russian, Database: CAPLUS
    EtSP(O)MeON:CClR (R = Me, Et, Pr) were prepd. in 42-47% yields by treating RCCl2NO with EtSPMeCl in the presence of SO2.
    
    
76. Alkoxycarbonylimines of hexafluoroacetone
    By Korenchenko, O. V.; Sokolov, V. B.; Aksinenko, A. Yu.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1990), (2), 373-5. Language: Russian, Database: CAPLUS
    Treating (CF3)2C(NCO)Cl with ROH (R = Pr, Bu, isopentyl, PhCH2) in Et2O followed by C5H5N in Et2O gave 55-67% (CF3)2C:NCO2R. Benzylation of (CF3)2C:NCO2CH2Ph (I) with PhCH2OH gave 64% PhCH2OC(CF3)2NHCO2CH2Ph; amination of I by 3,4-ClFC6H3NH2 gave 95% 3,4-ClFC6H4NHC(CF3)2NHCO2CH2Ph. Addn. of (CF3)2CO to H2NCO2Et gave 100% (CF3)2C(OH)NHCO2Et which was hydrolyzed to give 74% (CF3)2C:NCO2Et.
    
    
77. O-(alkylchloroformimino)(methyl)thiophosphonic acid chlorides
    By Lyashenko, Yu. E.; Sokolov, V. B.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1989), (12), 2865-6. Language: Russian, Database: CAPLUS
    Treating the adduct from RCCl2NO and MePCl2 with H2S gave 21-35% MeP(S)ClON:CRCl.
    
    
78. Interaction of phosphorus-containing cyanoguanidines with imines of hexafluoroacetone
    By Aksinenko, A. Yu.; Sokolov, V. B.; Korenchenko, O. V.; Chekhlov, A. N.; Fokin, E. A.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1989), (12), 2815-19. Language: Russian, Database: CAPLUS
    Cyclization of (EtD)2P(O)CMeRNHC(NH2):NCN (R = Me, Et) with (CF3)2C:NCOR1 (R1 = CF3, OEt, Me) gave 40-86% oxadiazines I.
    
    
79. Potential function of internal rotation for (CH3)2CClNO (2-chloro-2-nitrosopropane), CH3CCl2NO (1,1-dichloro-1-nitrosoethane), and their deuterated derivatives
    By Trepalin, S. V.; Yarkov, A. V.; Sokolov, V. B.; Ivanov, A. N. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1990), (3), 550-5. Language: Russian, Database: CAPLUS
    Conformational potential functions for the Cl-C-NO dihedral angle system (with 0° corresponding to cis Cl-NO, 180° corresponding to trans) in (CH3)2CClNO (I) and CH3CCl2NO (II) were detd. by IR anal. The cis-trans conformational potential barrier in I was 1876 cm-1, with a conformational energy max. at 86°; the cis(Cl)-cis(Cl) barrier in II was 702 cm-1, and the cis(Cl)-cis(Me) barrier was 1124 cm-1.
    
    
80. Synthesis of O-substituted acethydroximoyl chlorides and structure of O-carbamoylacethydroximoyl chloride
    By Sokolov, V. B.; Chekhlov, A. N.; Epishina, T. A.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1989), (12), 2849-51. Language: Russian, Database: CAPLUS
    Treating MeCCl2NO (I) with Me3SiCl and Zn in Et2O gave 52% E- and Z-MeCCl:NOSiMe3, which condensed with COCl2 at 70-80° in a sealed vessel to give 73% E- and Z-MeCCl:NO2CCl. Amidating this mixt. with excess NH3 and Et2O gave 61% E- and Z-MeCCl:NO2CNH2 (II) (23% overall yield from I). X-ray crystallog. of II indicated a trans conformation.
    
    
81. Method for obtaining (2,2-dichlorovinyl)dichlorophosphine oxide
    By Martynov, I. V.; Kolbasenko, S. I.; Sokolov, V. B. From U.S.S.R. (1990), SU 1549954 A1 19900315. Language: Russian, Database: CAPLUS
    Cl2C:CHP(O)Cl2 was prepd. by reaction of POCl3 with Cl3CCHO in the presence of a Zn-Cu couple in refluxing Et2O.
    
    
82. Interaction of a phosphorus-containing N-(trifluoromethyl)fluoroformamidine with methylamine
    By Levkovskii, A. V.; Aksinenko, A. Yu.; Pushin, A. N.; Sokolov, V. B.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1989), (12), 2868. Language: Russian, Database: CAPLUS
    Reaction of (EtO)2P(O)CMe2NMe(CF:NCF3) with MeNH2 in Et2O gave 26% (formamidiniumimino)oxidooxodiazaphospholine I.
    
    
83. Reaction of chlorohexafluoroisopropyl isocyanate with O-(chloroisobutyriminoxy)trimethylsilane
    By Sokolov, V. B.; Korenchenko, O. V.; Epishina, T. A.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1989), (10), 2390. Language: Russian, Database: CAPLUS
    Reaction of ClC(CF3)2NCO with Me3SiON:CClCHMe2 8 h at 180° gave 57.7% E- and Z-Me2CHCCl:NOC(CF3)2NCO.
    
    
84. Vibrational spectra and conformational equilibrium of 1,1-dichloro-1-nitrosoethane and its deuterium analog
    By Trepalin, S. V.; Yarkov, A. V.; Sokolov, V. B.; Ivanov, A. N.; Aksinenko, N. A.; Fetisov, V. I. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1989), (11), 2536-40. Language: Russian, Database: CAPLUS
    A vibrational anal. was presented for RCCl2NO (R = Me, CD3). Two conformers were present, the more stable having cis Cl-C and N:O bonds.
    
    
85. O-Substituted alkylchloroformoximes as substrates and inhibitors of cholinesterases
    By Ivanov, Yu. Ya.; Sokolov, V. B.; Epishina, T. A.; Martynov, I. V. From Doklady Akademii Nauk SSSR (1990), 310(5), 1253-5 [Biochem.]. Language: Russian, Database: CAPLUS
    The ability of O-substituted alkylchloroformoximes to serve as substrates for acetylcholinesterase (ACE, EC 3.1.1.7) and butyrylcholinesterase (BCE, EC 3.1.1.8) and to inhibit acetylcholine hydrolysis by these enzymes was detd., along with the LD50 of these compds. in mice. The compds. tested were O-acylated alkylchloroformoximes of the general formula R1C(O)ON:C(Cl)R2 [R1 = R2 = Me; R1 = Me, R2 = Et; R1 = Me, R2 = Pr; R1 = Et, R2 = Me; R1 = Et, R2 = iso-Pr; R1 = Pr, R2 = iso-Pr; R1 = CH2Cl, R2 = Pr (I); R1 = CH2Cl, R2 = iso-Pr (II)], O-carbonylated alkylchloroformoximes of the general formula EtOC(O)ON:C(Cl)R [R = Me (III), iso-Pr (IV)], and O-carbamoylated alkylchloroformoximes of the general formula (Me)2NC(O)ON:C(Cl)R [R = Me (V), iso-Pr (VI)]. All of the compds. except for I and II were good substrates for the enzymes, with Km values for ACE ranging (0.3-11.0) ? 10-4M and for BCE ranging (0.5-13.0) ? 10-4M (the Km values of ACE and BCE with acetylcholine were 1.3 ? 10-4 and 5.4 ? 10-4M, resp.). III and IV were competitive (Ki 1.6 ? 10-4M) and mixed-type (Ki 4.2 ? 10-4M) inhibitors, resp., of ACE. V and VI were effective inhibitors of both ACE and BCE, with bimol. rate consts. for inhibition (kII) of 5.7 ? 103 and 1.4 ? 105 M-1 min-1, resp., for ACE, and 9.8 ? 103 and 5.4 ? 106 M-1 min-1, resp., for BCE. The LD50 values for the tested compds. ranged 60-381 mg/kg body wt.
    
    
86. Diethoxythiophosphoryl-1,2-dichloroacetaldoxime possessing fungicidal activity By Martynov, I. V.; Ivanov, A. N.; Epishina, T. A.; Sokolov, V. B.; Beznosko, B. K.; Kissa, G. A.; Andreeva, E. I.; Monova, V. I.; Zaikin, B. A.; et al.
    From U.S.S.R. (1989), SU 1525159 A1 19891130. Language: Russian, Database: CAPLUS
    (EtO)2P(S)ON:CClCH2Cl has fungicidal activity.
    
    
87. Synthesis and structure of O,O-dialkyl 2-[(ethoxycarbonyl)amino]hexafluoroisopropylphosphonates
    By Aksinenko, A. Yu.; Chekhlov, A. N.; Korenchenko, O. V.; Sokolov, V. B.; Martynov, I. V. From Zhurnal Obshchei Khimii (1990), 60(1), 61-5. Language: Russian, Database: CAPLUS
    The title compds. (RO)2P(O)C(CF3)2NHCO2Et (I; R = Me, Et, CHMe2) were prepd. in 54-76% yields in the reaction of (RO)2P(O)H with (CF3)2C:NCO2Et. The crystal and mol. structure of I (R = Et) was detd.
    
    
88. Interaction of chloronitrosoalkanes with diphenylphosphinous acid trimethylsilyl ester
    By Sokolov, V. B.; Ivanov, A. N.; Epishina, T. A.; Goreva, T. V.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1990), (2), 476-7. Language: Russian, Database: CAPLUS
    Phosphorylated oximes Ph2P(O)ON:CRR' (R = alkyl; R' = Cl, Me) were formed in 37-44% yields in the Allen reaction (1957) of trimethylsilyl ester Ph2POSiMe3 with RR'ClCN:O.
    
    
89. Reaction of N-substituted cyanoguanidines with hexafluoroacetone
    By Martynov, I. V.; Aksinenko, A. Yu.; Chekhlov, A. N.; Korenchenko, O. V.; Torgun, I. N.; Sokolov, V. B. From Zhurnal Obshchei Khimii (1989), 59(6), 1397-400. Language: Russian, Database: CAPLUS
    Cycloaddn. reaction of RNHC(NH2):NCN [R = Me3C, Ph, (R1O)2P(O)CMeR2; R1 = Me, R2 = Me, Et; R1 = Et, R2 = Et, Pr] with (CF3)2CO in Et2O at -15 to -10° gave 4 corresponding guanidinodioxazines I [R3 = H, HOC(CF3)2] in 49-94% yield and 62-97% aminotriazinones II [R = Ph, (EtO)2P(O)CMeEt]. Refluxing I (same R, R3) 6 h in C6H6 gave the corresponding II in 56-89% yield.
    
    
90. Synthesis and cholinesterase hydrolysis of O-acylated alkylchloroformoximes
    By Sokolov, V. B.; Ivanov, Yu. Ya.; Epishina, T. A.; Agabekyan, R. S.; Martynov, I. V. From Khimiko-Farmatsevticheskii Zhurnal (1989), 23(11), 1317-20. Language: Russian, Database: CAPLUS
    The title compds., RCO2N:CClR1 (R = Me, Et, Pr or CH2Cl and R1 = Me, Et, Pr, or iso-Pr) were prepd. e.g., by the reaction of 1,1-dichloro-1-nitrosobutane with AcCl in the presence of Zn. These compds. were good substrates for acetyl- and butyrylcholinesterases. The kinetic parameters (Km, Vmax and ac) of these compds. in the hydrolysis reactions were comparable to those with acetylcholine. The acute toxicity was 79-381 mg/kg in mice given drugs orally.
    
    
91. Crystal and molecular structure of 2-ethoxy-2-oxo-3,3,4-trimethyl-5-(cyanimino)-1,4,2-diazaphospholan
    By Chekhlov, A. N.; Levkovskii, A. V.; Aksinenko, A. Yu.; Sokolov, V. B.; Martynov, I. V. From Doklady Akademii Nauk SSSR (1989), 309(6), 1410-13 [Phys. Chem.]. Language: Russian, Database: CAPLUS
    The title compd. is monoclinic, space group P21/c, with a 0.164(1), b 14.654(5), c 8.607(5) A, and ? 92.65(2)°; dc = 1.324 for Z = 4. The at. coordinates are given. The structure was solved by direct methods and refined by least-squares to R = 0.050. The bond lengths and angles are given.
    
    
92. Vibrational spectra and conformational equilibrium of (CH3)2CClNO and (CD3)2CClNO
    By Trepalin, S. V.; Yarkov, A. V.; Sokolov, V. B.; Ivanov, A. N.; Aksinenko, N. A.; Fetisov, V. I. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1989), (7), 1538-44. Language: Russian, Database: CAPLUS
    Vibrational spectroscopy (IR and Raman) was used to identify the conformational equil. in Me2CClNO (I) as one involving eclipsed (Cs) and trans (Cs) Cl-C-N:O conformers, with heat of conformational inversion of 1.22 kcal/mol.; the eclipsed conformer was calcd. to be the lowest energy conformer (MNDO). The force field derived from the vibrational spectra of I and I-d6 reproduced the vibrational spectra of I isotopomers with mean square deviation of 8.4 cm-1, max. deviation of 22 cm-1.
    
    
93. Reaction of 1,1-dichloro-1-nitrosobutane with (N,N-dimethylamido)dichlorophosphite
    By Sokolov, V. B.; Ivanov, A. N.; Epishina, T. A.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1989), (6), 1416-18. Language: Russian, Database: CAPLUS
    Reaction of PrCCl2NO with Me2NPCl2 in Et2O or in SO2 gave 36% Me2NPCl4 or 30% Me2NP(O)ClON:CClPr, resp. Treating Me2NPCl4 with SO2 gave 91% Me2NP(O)Cl2. Reaction of PrCCl2NO with Me2NPCl2 in Et2O, and then with Ph3P and distn. gave Ph3PO and PrCN.
    
    
94. Interaction of methyldichlorophosphine with the ethoxycarbonylimine of hexafluoroacetone in sulfur dioxide
    By Sokolov, V. B.; Aksinenko, A. Yu.; Korenchenko, O. V.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1989), (5), 1213. Language: Russian, Database: CAPLUS
    Oxazaphospholine I, formed quant. in the reaction of MePCl2 with EtO2CN:C(CF3)2, was highly prone to C-O ring cleavage with OH, NH, and SH nucleophiles.
    
    
95. Effect of fluoride hyperconjugation in the structure of diethyl 1-[[(N,N-diisopropylfluoroformamidino)carbonyl]amino]-1-methylpropylphosphonate
    By Chekhlov, A. N.; Aksinenko, A. Yu.; Sokolov, V. B.; Martynov, I. V. From Doklady Akademii Nauk SSSR (1989), 304(2), 400-4 [Phys. Chem.]. Language: Russian, Database: CAPLUS
    The structure of (EtO)2P(O)CMeEtNHCON:CFN(CHMe2)2 was detd. by x-ray crystallog. The N-C-N angle in the -N:CFN(CHMe)2 fragment is 15° greater than the ideal trigonal angle of 120°, indicating a fairly strongly neg. hyperconjugative effect from the F.
    
    
96. Molecular structure of new heterocyclic compounds of 6-coordinate phosphorus cyclic-F4PC (RR1) NHC(NR22)NH
    By Chekhlov, A. N.; Martynov, I. V.; Aksinenko, A. Yu.; Sokolov, V. B. From Koordinatsionnaya Khimiya (1989), 15(9), 1192-8. Language: Russian, Database: CAPLUS
    I is monoclinic, space group P2q/C, with a 10.390(3),b 11.790(2), c 12.749(2) A°, and B 94.84(2)°; Z = 4. The at. parameters are given. The structure was solved by direct methods and refined by full-matrix least-squares to R = 0.045. The bond lengths and angles are given. The results are compared with those detd. earlier for related compds.
    
    
97. Reaction of hexafluroacetonimine with phosphorus-hydrogen acids
    By Martynov, I. V.; Aksinenko, A. Yu.; Chekhlov, A. N.; Sokolov, V. B. From Zhurnal Obshchei Khimii (1989), 59(4), 809-11. Language: Russian, Database: CAPLUS
    Reaction of (CF3)2C:NH with R2P(O)H (R = Ph, PhCH2) in C6H6 gave 63-65% phosphine oxides R2P(O)C(CF3)2NH (I; same R), whereas reaction with MeCHCH2OP(O)HMe gave 55% methylphosphinate Me2CHCH2OP(O)MeC(CF3)2NH2. Treating I (R = PhCH2) with ketene (CF3)2C:CO gave 48% R2P(O)C(CF3)2NHCOCH(CF3)2.
    
    
98. Influence of synthetic inhibitors of proteinases on the level of production of recombinant human proinsulin secreted by a genetically engineered culture Bacillus subtilis
    By Parfenova, E. V.; Popov, D. G.; Novikov, A. A.; Sterkin, V. E.; Strongin, A. Ya.; Aksinenko, A. Yu.; Korenchenko, O. V.; Fetisov, V. I.; Martynov, I. V.; Sokolov, V. B. From Bioorganicheskaya Khimiya (1989), 15(7), 987-9. Language: Russian, Database: CAPLUS
    O,O-Diethyl-1-(N-hydrohexafluoroisobutyryl)amino-1-methylpropylphosphonate and O,O-diisobutyl-1-[2-(ethoxycarbonyl)aminoperfluoroprop-2-yl]-1-methylpropylphosphonate, which are nontoxic to microorganisms, decreases the degrdn. of proinsulin by serine proteinases thereby increasing human proinsulin secretion by genetically engineered culture of Bacillus sustilis A4 73 (pBINS1.0).
    
    
99. X-ray structural study of 1-oxo-4-isopropyl- and 1-thio-4-propyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane
    By Chekhlov, A. N.; Sokolov, V. B.; Fetisov, V. I.; Martynov, I. V. From Zhurnal Strukturnoi Khimii (1989), 30(3), 108-13. Language: Russian, Database: CAPLUS
    The title oxo compd. is orthorhombic, space group Pnma with a 12.390(1)8 b 9.542(2), and c 7.331(2) A; dc = 1.473 for Z = 4. The title thio compd. is monoclinic, space group P21/m, with a 7.787(1), b 9.211(2), c 7.208(3) A, and ? 104.72(3)°; dc = 1.383 for Z = 2. The at. coordinates are given. The structures were solved by the MULTAN program and refined by full-matrix least-squares to R = 0.10 and 0.02, resp. The bond lengths and angles are given.
    
    
100. Molecular and crystal structure of O,O-diethyl 1-[N2-(trifluoromethyl)fluoroformamidino]-1-methylethylphosphonate
     By Chekhlov, A. N.; Aksinenko, A. Yu.; Sokolov, V. B.; Korenchenko, O. V.; Martynov, I. V. From Doklady Akademii Nauk SSSR (1988), 302(4), 855-8 [Chem.]. Language: Russian, Database: CAPLUS
     The crystal and mol. structure of (EtO)2P(O)CMe2NHCFNCF3 was detd.
     
     
101. Synthesis and NMR spectra of 5-dialkylamino-2,2,2,2-tetrafluoro-?5-1,4,2?6-diazaphosphoratolines
     By Martynov, I. V.; Aksinenko, A. Yu.; Pushin, A. N.; Chekhlov, A. N.; Fokin, E. A.; Sokolov, V. B. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1988), (9), 2123-8. Language: Russian, Database: CAPLUS
     Cyclizing (RO)2P(O)CMeR1N:C:NCF3 (R = Me, Et; R1 = Me, Et, Me2CHCH2) with R22NH (R2 = Et, Pr, Me2CH) gave 23-47% of 7 title compds. I.
     
     
102. O-(Alkylchloroformimidoyl) o-alkyl methylphosphonates
     By Sokolov, V. B.; Ivanov, A. N.; Goreva, T. V.; Epishina, T. A.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1988), (5), 1128-30. Language: Russian, Database: CAPLUS
     Nine (RO)MeP(O)ON:CClR1 (R = Et, Pr, Bu, Me2CH, pentyl; R1 = Me, Et, Pr, Bu, Me2CH) were prepd. in 41-67% yields by treating R1CCl2NO with MeP(OR)2 or MeP(O)H(OR).
     
     
103. Reaction of 1,1-dichloro-1-nitrosoalkanes with trimethylchlorosilane and zinc
     By Sokolov, V. B.; Epishina, T. A.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1989), (3), 745. Language: Russian, Database: CAPLUS
     Treating RCCl2NO (R = Me, Pr, Me2CH) with Me3SiCl and Zn dust in Et2O gave 16-33% Me3SiON:CRCl as mixts. of isomers.
     
     
104. O-Amylmethylphosphonyl-O-alkylchloroformoximes displaying aphicidal activity
     By Martynov, I. V.; Ivanov, A. N.; Epishina, T. A.; Goreva, T. V.; Sokolov, V. B.; Zhuravleva, V. I.; Syrova, L. M.; Beznosko, B. K. From U.S.S.R. (1989), SU 1456439 A1 19890207. Language: Russian, Database: CAPLUS
     O-Amylmethylphosphonyl-O-alkylchloroformoximes (sic) (I; R = Me, iso-Pr) have aphicidal activity.
     
     
105. X-ray studies on (1-aminohexafluoroisopropyl)diphenylphosphine oxide
     By Chekhlov, A. N.; Aksinenko, A. Yu.; Sokolov, V. B.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1988), (11), 2622-4. Language: Russian, Database: CAPLUS
     The crystal and mol. structure of Ph2P(O)C(CF3)2NH2 (I) was detd. I has intramol. N-H•••F-C hydrogen bonding.
     
     
106. Phosphorus-containing N-(trifluoromethyl)ureas and their reactions with secondary amines
     By Martynov, I. V.; Aksinenko, A. Yu.; Korenchenko, O. V.; Gontar, A. F.; Sokolov, V. B. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1988), (11), 2618-20. Language: Russian, Database: CAPLUS
     (RO)2P(O)CMeR1NHCONHCF3 (I, R = R1 = Me, Et; R = Me, R1 = Et) were prepd. in 30-70% yields by treating (RO)2P(O)CMeR1N:C:NCF3 with H2O at 20°. Treating I with R22NH (R2 = Et, Pr, Me2CH) gave 50-73% (RO)2P(O)CMeR1NHCON:CFNR22.
     
     
107. Reaction of 1,1-dichloro-1-nitrosoalkanes with phosphorus(III) chlorides
     By Martynov, I. V.; Ivanov, A. N.; Epishina, T. A.; Sokolov, V. B. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1988), (9), 2128-32. Language: Russian, Database: CAPLUS
     The title reaction was studied. Thus, R1R2P(O)ON:CRCl (R = Me, Et, Pr, Me2CH; R1 = R2 = Cl, Me2CHCH2; R1 = Cl, R2 = Me) were prepd. in 34-74% yields by reaction of RCCl2NO with R1R2PCl in the presence of SO2.
     
     
108. X-ray structural study of the final products from the reaction of O,O-diethyl-1-(2-cyanoguanidino)-1-methylpropylphosphonate with trifluoroacetylimine hexafluoroacetone
     By Chekhlov, A. N.; Aksinenko, A. Yu.; Korenchenko, O. V.; Sokolov, V. B.; Martynov, I. V. From Doklady Akademii Nauk SSSR (1988), 302(1), 107-11 [Chem.]. Language: Russian, Database: CAPLUS
     The crystal structure of the oxadiazine I from the title reaction was detd.
     
     
109. Reaction of phosphorus-containing N-(trifluoromethyl)fluoroamidines with nitrogen nucleophiles
     By Martynov, I. V.; Aksinenko, A. Yu.; Korenchenko, O. V.; Chekhlov, A. N.; Fokin, E. A.; Sokolov, V. B. From Zhurnal Obshchei Khimii (1988), 58(9), 2165-7. Language: Russian, Database: CAPLUS
     Treating (EtO)2P(O)CMe2NHCF:NCF3 with NH3 in MeCN or with Et2NH in Et2O gave 74% (EtO)2P(O)CMe2NHC(NH2):NCN or 61% hydrodiazaphosphole I, resp.
     
     
110. Interaction of phosphorus-containing N2-(trifluoromethyl)-N1-methylfluoroamidine with ammonia
     By Aksinenko, A. Yu.; Sokolov, V. B.; Korenchenko, O. V.; Pushin, A. N.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1988), (7), 1688-89. Language: Russian, Database: CAPLUS
     Treating (EtO)2P(O)CMe2NMeCF:NCF3 with NH3 gave (EtO)(H2N)P(O)CMe2NMeC(NH2):NCN which cyclizes to diazaphospholidine I at 80°.
     
     
111. Reaction of 1,1-dichloro-1-nitrosoethane with phosphorus oxychloride in the presence of zinc
     By Sokolov, V. B.; Epishina, T. A.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1988), (7), 1691. Language: Russian, Database: CAPLUS
     Cl2P(O)ON:CClMe was prepd. in 26.6% yield by treating MeCCl2NO with POCl3 in the presence of Zn.
     
     
112. Reaction of N-substituted N'-(trifluoromethyl)carbodiimides with ammonia
     By Martynov, I. V.; Aksinenko, A. Yu.; Korenchenko, O. V.; Gontar, A. F.; Sokolov, V. B. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1988), (10), 2399-400. Language: Russian, Database: CAPLUS
     Carbodiimides RN:C:NCF3 (R = tert-Br, aryl) react with NH3 to form cyanoguanidines RNHC(NH2):NC?N in yields < 94%.
     
     
113. A convenient preparative method for the synthesis of chlorohexafluoropropyl isocyanate
     By Sokolov, V. B.; Korenchenko, O. V.; Aksinenko, A. Yu.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1988), (9), 2189. Language: Russian, Database: CAPLUS
     Title compd. (CF3)2CClNCO was prepd. in 70% yield by treatment of imine (CF3)2C:NCO2Et with PCl5 for 2 h at 100°.
     
     
114. Comparative studies on the interaction of acetylcholinesterases from human erythrocytes and housefly heads with phosphorylated alkylchloroformoxims
     By Shataeva, G. A.; Makhaeva, G. F.; Yankovskaya, V. L.; Sokolov, V. B.; Ivanov, A. N.; Martynov, I. V. From Zhurnal Evolyutsionnoi Biokhimii i Fiziologii (1988), 24(6), 791-6. Language: Russian, Database: CAPLUS
     Among Valexon analogs, 6 (RO)2P(O)ON:CClMe (I), 6 (RO)2P(O)ON:C(Cl)CH2Cl (II), and 5 (RO)2P(O)ON:C(Cl)CHCl2 (III, R = Me, Et, Pr, iso-Bu, Bu, amyl), and 4 (EtO)2P(O)ON:C(Cl)R1 (IV, R1 = Me, Et, Pr, Bu), I-III (R = Et) were highly selective insecticides, having rate consts. of bimol. reaction with acetylcholinesterase (KII) of human erythrocytes (HE) lower by 1 magnitude order than with that from housefly heads (FL). Inhibition of both HE and FL followed the order I < II < III. Phosphorylation capacity of II 1.6-fold exceeded that of I. Replacing Me by Et, increased the effect of I-III on FL 3-8-fold and decreased that on HE 1.7-4-fold. Further increases in hydrophobicity abolished the specificity of I-III. The selectivity of IV decreased in order of R1: Me > Et > Bu; IV (R1 = Pr) showed no selectivity.
     
     
115. Molecular and crystal structure of a hexacoordinate phosphorus compound
     By Chekhlov, A. N.; Martynov, I. V.; Aksinenko, A. Yu.; Sokolov, V. B. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1988), (4), 936-7. Language: Russian, Database: CAPLUS
     The crystal and mol. structure of the 6-coordinate P compd. I (one of 3-tautomeric forms shown) was detd. by x-ray anal. The coordination of the P atom is distored octahedral.
     
     
116. O-(Alkylchloroformimino) O,O-dialkyl thiophosphates
     By Martynov, I. V.; Ivanov, A. N.; Epishina, T. A.; Sokolov, V. B. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1987), (12), 2854-5. Language: Russian, Database: CAPLUS
     Seven (RO)2P(S)ON:CClR1 (R = Et, Me2CH; R1 = Me, Et, Pr, Me2CH, ClCH2) were prepd. in 33-54% yields by condensing (RO)2PSH with R1Cl2CNO in THF.
     
     
117. Electron donor and acceptor functions of physiologically active compounds and model compounds. XI. Effect of alkyl substituents in phosphorylated oximes on their complexation with deuteriochloroform
     By Raevskii, O. A.; Chapysheva, N. V.; Ivanov, A. N.; Sokolov, V. B.; Martynov, I. V. From Zhurnal Obshchei Khimii (1987), 57(12), 2720-3. Language: Russian, Database: CAPLUS
     (RO)2P(O)ON:CClR1 (I; R = Et, R1 = Me, Et, Pr, Me2CH, Bu; R = Me, R1 = Et) were prepd. in 44-66% yields by treating (RO)3P with ONCCl2R1. The thermodn. parameters for the complexation of I with CDCl3 were detd. spectrophotometrically.
     
     
118. Unusual synthesis and structure of new compounds of 6-coordinate phosphorus with a 5-membered C2N2P ring
     By Martynov, I. V.; Chekhlov, A. N.; Aksinenko, A. Yu.; Sokolov, V. B.; Pushin, A. N. From Doklady Akademii Nauk SSSR (1987), 297(5), 1132-6 [Chem.]. Language: Russian, Database: CAPLUS
     The title compds. I (R1, R2 = Me, Et; R3 = Et, Pr, Me2CH) were prepd. by cyclizing (RO)2P(O)CR1R2N:C:NCF3 (R = Me, Et) with R32NH. The crystal structure of I (R1 = R2 = Me, R3 = Et) was detd.
     
     
119. Synthesis and structure of phosphorus-containing cyanoguanidines
     By Martynov, I. V.; Chekhlov, A. N.; Aksinenko, A. Yu.; Pushin, A. N.; Sokolov, V. B.; Gontar, A. F. From Zhurnal Obshchei Khimii (1987), 57(10), 2285-9. Language: Russian, Database: CAPLUS
     (RO)2P(O)CMeR1NHC(NH2):NCN [R = Me, R1 = Et; R = R1 = Et; R = Et, R1 = Pr (I)] were prepd. in 54-90% yields by treating (RO)2P(O)CMeR1N:C:NCF3 with NH3. The crystal structure of I was detd.
     
     
120. Synthesis and molecular structure of (O-isopropylchloroformimino) diphenylphosphinate
     By Martynov, I. V.; Chekhlov, A. N.; Ivanov, A. N.; Epishina, T. A.; Makhaev, V. D.; Sokolov, V. B. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1987), (11), 2595-7. Language: Russian, Database: CAPLUS
     Treating Ph2PH with Me2CHCCl2NO in C6H6 gave 58% Ph2P(O)ON:CClCHMe2, the structure of which was detd. by x-ray crystallog.
     
     
121. Reaction of diisobutylchlorophosphine with 1,1-dichloro-1-nitrosoalkanes in presence of sulfur dioxide and ethyl mercaptan
     By Sokolov, V. B.; Ivanov, A. N.; Epishina, T. A.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1987), (11), 2586-8. Language: Russian, Database: CAPLUS
     Treating (Me2CHCH2)2PCl with RCCl2NO (R = Me, Et, Pr, Me2CH) in Et2O contg. SO2 gave 61-74% (Me2CHCH2)2P(O)ON:CRCl (same R). When Et2SH was used instead of SO2, 44% (Me2CHCH2)2P(S)ON:CRCl (R = Me) was obtained.
     
     
122. Crystal and molecular structure of O,O-diethyl 1-[2(1H)-oxo-3,4-dihydro-4,4-bis(trifluoromethyl)-1,3,5-triazin-6-yl]amino-1-methylpropylphosphonate
     By Chekhlov, A. N.; Aksinenko, A. Yu.; Sokolov, V. B.; Korenchenko, O. V.; Martynov, I. V. From Doklady Akademii Nauk SSSR (1988), 300(3), 658-61 [Phys. Chem.]. Language: Russian, Database: CAPLUS
     The title compd. is monoclinic, space group P21/c, with a 11.539(8), b 20.798(12), c 8.385(6) A, and ? 97.63(6)°; dc = 1.473 for Z = 4. The at. parameters are given. The structure was solved by direct methods and refined by full-matrix least-squares to R = 0.0726 and Rw = 0.0926. The P atom is in a distorted tetrahedral configuration. The bond lengths and angles are given.
     
     
123. Electron-donor and -acceptor functions of physiologically active and model compounds. X. Electron-donor functions of ethyl methylchloroformimino methylphosphonate
     By Raevskii, O. A.; Grigor'ev, V. Yu.; Solov'ev, V. P.; Ivanov, A. N.; Sokolov, V. B.; Martynov, I. V. From Zhurnal Obshchei Khimii (1987), 57(9), 2073-8. Language: Russian, Database: CAPLUS
     Equil. consts. and thermodn. functions were detd. by IR spectral and calorimetry methods for the H bonding of (EtO)P(O)MeON:CMeCl (I) with EtOH, Ph2NH, PhNH2, and Et carbamate. The important role of the oxime group in complexation was revealed.
     
     
124. New compounds of hexacoordinated phosphorus
     By Martynov, I. V.; Aksinenko, A. Yu.; Chekhlov, A. N.; Pushin, A. N.; Sokolov, V. B. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1987), (7), 1680. Language: Russian, Database: CAPLUS
     Cyclic phosphoranes I (R = Me, Et, Me2CHCH2; R1 = Et, Pr, Me2CH) were prepd. in 33-47% yields by cyclizing (EtO)2P(O)CMeRN:C:NCF3 with R12NH.
     
     
125. Interaction of 2,2,3,3-tetrafluoropropyl dichlorophosphite with 1,1,2-trichloro-1-nitrosoethane
     By Sokolov, V. B.; Ivanov, A. N.; Epishina, T. A.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1987), (6), 1422-3. Language: Russian, Database: CAPLUS
     Refluxing CHF2CF2CH2OPCl2 (I) with CH2ClCCl2NO (II) in Et2O gave 67.8% Cl2P(O)ON:CClCH2Cl. Treating I with II in SO2 at 20° gave 48.2% (CHF2CF2CH2O)ClP(O)ON:CClCH2Cl.
     
     
126. Reaction of dichloromethylphosphine with 1,1-dichloro-1-nitrosoalkanes
     By Sokolov, V. B.; Ivanov, A. N.; Epishina, T. A.; Martynov, I. V. From Zhurnal Obshchei Khimii (1987), 57(7), 1659-60. Language: Russian, Database: CAPLUS
     MePCl2 reacted with RCCl2NO (R = Et, Pr, Me2CH) in SO2 to give 27-37% RCCl:NOP(O)ClMe.
     
     
127. Reaction of polychloronitrosoethanes with phosphorous acid derivatives
     By Martynov, I. V.; Ivanov, A. N.; Epishina, T. A.; Sokolov, V. B. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1987), (5), 1086-9. Language: Russian, Database: CAPLUS
     The title reaction gave 20-93% of 22 o-phosphorylated alkyl chloroformimines. Thus, treating ONCCl2R (R = Me, CH2Cl, CHCl2) with (R1O)3P (R1 = Me, Pr, Bu, Me2CHCH2, pentyl, ClCH2CH2) gave (R1O)2P(O)ON:CClR.
     
     
128. Reactions of methyl 2-imino-3,3,3-trifluoropropionates with CH- and PH-acids
     By Osipov, S. N.; Sokolov, V. B.; Kolomiets, A. F.; Martynov, I. V.; Fokin, A. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1987), (5), 1185-8. Language: Russian, Database: CAPLUS
     The reaction of (MeO2C)C(CF3):NR (I; R = SO2Ph, COCF3) with R1H [R1 = R2COCHCOR3 (R2 = R3 = Me, EtO; R2 = Me, R3 = EtO), (R4O)2P(O) (R4 = Me, Et, pentyl, Ph)] gave (MeO2C)C(CF3)(NHR)R1. The reactivity is dependent on the nature of I and R1H.
     
     
129. Reaction of (aminoalkyl)phosphonates with perfluoro-2-azapropene
     By Aksinenko, A. Yu.; Pushin, A. N.; Sokolov, V. B.; Gontar, A. F.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1987), (5), 1177-9. Language: Russian, Database: CAPLUS
     (RO)2P(O)CMeR1N:C:NCF3 (R = Me, R1 = Et; R = Et, R1 = Et, Pr, Bu; R = Me2CHCH2, R1 = Et) were prepd. in 40-60% yields by condensing CF2:NCF3 with (RO)2P(O)CMeR1(NH2) in the presence of KF.
     
     
130. Reaction of diphenylphosphinous acid with 1,1-dichloro-1-nitrosoalkanes
     By Sokolov, V. B.; Epishina, T. A.; Ivanov, A. N.; Kharitonov, A. V.; Brel, V. K.; Martynov, I. V. From Zhurnal Obshchei Khimii (1987), 57(7), 1658-9. Language: Russian, Database: CAPLUS
     Treating Ph2P(O)H with RCCl2NO (R = Et, Pr, Me2CH) in Et2O gave 62-75% Ph2P(O)ON:CClR (same R).
     
     
131. Reaction of O-alkyl methylphosphonites with 1,1-dichloro-1-nitrosopropane
     By Sokolov, V. B.; Ivanov, A. N.; Epishina, T. A.; Martynov, I. V. From Zhurnal Obshchei Khimii (1987), 57(4), 952-3. Language: Russian, Database: CAPLUS
     Reaction of ROP(O)HMe (R = Me2CH, Bu, pentyl) with EtCCl2NO in Et2O gave 50-52% ROP(O)MeON:CClEt (I; same R). Treating MeP(OR)2 with EtCCl2NO also gave I.
     
     
132. Reaction of dialkyl phosphites with 1,1-dichloronitrosoalkanes
     By Ivanov, A. N.; Epishina, T. A.; Goreva, T. V.; Sokolov, V. B.; Martynov, I. V. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1987), (1), 226-8. Language: Russian, Database: CAPLUS
     (RO)2P(O)ON:CClR1 (R = Bu, Me2CHCH2, pentyl, Me, Et; R1 = Me, Et, Pr, Me2CH, Bu, Me2CHCH2) were prepd. in 44-67% yields by treating (RO)2POH with ONCCl2R1 in EtOH at 20°.
     
     
133. Reaction of phosphorus trichloride with 1,1,2-trichloro-1-nitrosoethane in sulfur dioxide
     By Martynov, I. V.; Ivanov, A. N.; Epishina, T. A.; Sokolov, V. B. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1986), (9), 2158. Language: Russian, Database: CAPLUS
     Reaction of ClCH2CCl2NO with PCl3 in SO2 gave 58% ClCH2CCl:NOP(O)Cl2.
     
     
134. S,S-Dialkyl O-iminodithiophosphates
     By Martynov, I. V.; Chepakova, L. A.; Brel, V. K.; Sokolov, V. B. From Zhurnal Obshchei Khimii (1986), 56(10), 2420-1. Language: Russian, Database: CAPLUS
     (RS)2P(O)ON:CMeR1 (R = Et, Pr, Bu, R1 = Cl; R = Et, R1 = Me) were prepd. in 29-40% yields by treating (RS)2POEt with R1MeClCNO in Et2O at -20 to -15°.
     
     
135. Reaction of diethyl thiophosphite with 1,1-dichloro-1-nitrosobutane
     By Martynov, I. V.; Chepakova, L. A.; Ivanov, A. N.; Epishina, T. A.; Brel, V. K.; Sokolov, V. B. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1986), (9), 2158-9. Language: Russian, Database: CAPLUS
     Reaction of (EtO)2PSH with ONCCl2Pr in Et2O gave 25% (EtO)2PSON:CClPr.
     
     
136. Interactions of binding sites for bicyclic phosphorus-containing esters, picrotoxin, and tritium-labeled-aminobutyric acid
     By Pervukhin, G. Ya.; Maslov, A. A.; Kotel'nikov, S. A.; Sokolov, V. B.; Fetisov, V. I.; Martynov, I. V. From Doklady Akademii Nauk SSSR (1987), 293(3), 736-9 [Biochem.]. Language: Russian, Database: CAPLUS
     Rat brain membrane prepns. were used to study the binding-site interactions of GABA, picrotoxin, and 6 phosphorus-contg. esters (4-Me, 4-Et, and 4-propyl-2,6-7-trioxa-1-phosphabicyclo[2.2.2]octane and their resp. octane-1-oxides). A model of the receptor complex is presented involving a 2-fold allosterism in the phosphoester-picrotoxin-GABA receptor triad.
     
     
137. Interaction of dialkyl (carbomethoxy-trifluoroethyl) phosphates with mammalian esterases
     By Makhaeva, G. F.; Fetisov, V. I.; Sokolov, V. B.; Yankovskaya, V. L.; Goreva, T. V.; Malygin, V. V.; Beznosko, B. K.; Galenko, T. G.; Kolomiets, A. F.; Martynov, I. V. From Bioorganicheskaya Khimiya (1987), 13(1), 33-7. Language: Russian, Database: CAPLUS
     The title compds. having the general formula (RO)2P(O)OCH(CF3)CO2Me (R = lower alkyl) were not hydrolyzed by carboxylesterase (from pig liver), but these compds. slowly and irreversibly inhibited human erythrocyte acetylcholinesterase (k2 = 102-104M-1•min-1). In contrast, butyrylcholinesterase from horse serum and carboxylesterase were effectively inhibited by all 8 compds. (k2 = 103-107M-1•min-1). Inhibition of carboxylesterase and butyrylcholinesterase increased with increasing hydrophobicity of the alkoxy groups; the branching at the position of the alkoxy groups resulted in sharp redn. in the inhibition const. for cholinesterase and change in the mechanism of inhibition of carboxylesterase. The compds. have low toxicity and with the exception of the iso-Bu deriv., the LD50s (for mice) exceeded 1000 mg/kg.
     
     
138. Reaction of 1,1,2-trichloro-2-nitrosoethane with cyclopentadiene
     By Martynov, I. V.; Pushin, A. N.; Epishina, T. A.; Sokolov, V. B. From Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1986), (4), 955-6. Language: Russian, Database: CAPLUS
     ClCH2CCl2NO added to cyclopentadiene to give one unspecified isomer of cyclopentene I.
     
     
139. Reaction of trimethylolaminomethane with cycloalkanones
     By Sokolov, V. B.; Kryukov, L. N.; Kolomiets, A. F.; Sokol'skii, G. A. From Zhurnal Organicheskoi Khimii (1979), 15(8), 1777-9. Language: Russian, Database: CAPLUS
     Treatment of (HOCH2)3CNH2 with RCOR1 [RR1 = (CH2)4, (CH2)5, (CH2)2CHMe(CH2)2] gave 80-90% azazoles I.. I [RR1 = (CH2)5] and P(OMe)3 gave 90% II.
     
     
140. Study of the structural determinants of acute and delayed neurotoxicity of O-phosphorylated oximes by molecular field topology analysis (MFTA)
     By Radchenko E V; Makhaeva G F; Sokolov V B; Palyulin V A; Zefirov N S From Doklady. Biochemistry and biophysics (2009), 429, 309-14. Language: English, Database: MEDLINE
     
     
141. Esterase profile and analysis of structure-inhibitor selectivity relationships for homologous phosphorylated 1-hydroperfluoroisopropanols
     By Makhaeva G F; Serebryakova O G; Boltneva N P; Galenko T G; Aksinenko A Yu; Sokolov V B; Martynov I V From Doklady. Biochemistry and biophysics (2008), 423, 352-7. Language: English, Database: MEDLINE
     
     
142. Modeling of the relationships between the structure of O-phosphorylated oximes and their anticholinesterase activity and selectivity using molecular field topology analysis (MFTA)
     By Radchenko E V; Makhaeva G F; Malygin V V; Sokolov V B; Palyulin V A; Zefirov N S From Doklady. Biochemistry and biophysics (2008), 418, 47-51. Language: English, Database: MEDLINE
     
     
143. Fluorinated alpha-aminophosphonates--a new type of irreversible inhibitors of serine hydrolases
     By Makhaeva G F; Malygin V V; Aksinenko A Yu; Sokolov V B; Strakhova N N; Rasdolsky A N; Richardson R J; Martynov I V From Doklady. Biochemistry and biophysics (2005), 400, 92-5. Language: English, Database: MEDLINE
     
     
144. A new inhibitor of pyrimidine phosphorylase
     By Dmitrieva N A; Molchan O K; Komissarov A A; Sokolov V B; Aksinenko A Iu; Pushin A N; Chekhlov A N; Debabov V G From Bioorganicheskaia khimiia (1998), 24(12), 920-5. Language: Russian, Database: MEDLINE
     5,5-Bis(hydroxymethyl)-2-oxo-[1-(2-trifluoromethyl)-3,3,3- trifluoropropionamido)-1-trifluoromethyl-2,2,2-trifluoroethyl- 1,3,2-dioxaphosphan (CA-423) is an in vitro inhibitor of the Escherichia coli uridine and thymidine phosphorylases. Unlike widely studied nucleoside analogues, this compound binds to the enzymes irreversibly. Its LD50 in mice was 40 mg/kg. Due to the involvement of pyrimidine phosphorylases in carcinogenesis and the relatively low toxicity of CA-423, it is promising for anticancer therapy.
     
     
145. Paradoxical toxic effect and antagonism of O-(N-arylcarbamoylated) acylhydroxymoylchloride cholinesterase inhibitors with calcium
     By Ivanov Iu Ia; Sokolov V B; Epishina T A; Martynov I V From Doklady Akademii nauk / [Rossiiskaia akademii nauk] (1993), 328(6), 744-6. Language: Russian, Database: MEDLINE
     
     
146. Inhibition of enzymatic activity of alpha-thrombin by low molecular weight synthetic inhibitor
     By Kireeva E G; Strukova S M; Dugina T N; Sokolov V B; Aksinenko A Iu From Biokhimii a (Moscow, Russia) (1992), 57(1), 21-6. Language: Russian, Database: MEDLINE
     The effect of the organophosphoric inhibitor, SA-152, on the fibrinogen-coagulating and TAME-esterase activity of bovine alpha-thrombin was studied. The irreversible inhibition constants (k11 = 1.1 x 10(4) M-1.min-1,Ki = 0.7 x 10(-4) M, k2 = 0.8 min-1 towards the coagulating activity and kII = 0.7 x 10(4) M-1.min-1, Ki = 0.3 x 10(-4) M, k2 = 0.2 min-1 towards the esterase activity) were determined. The SA-152 inactivated alpha-thrombin was dialyzed and incubated with 0.5 M and 2.5 M NaCl and 10 mM TAME. There was no reconstitution of activity of the SA-152 modified alpha-thrombin after dialysis and treatment with high concentrations of NaCl and TAME. Heparin interactions with the anion-binding site of the high molecular weight recognition center in the alpha-thrombin molecule did not significantly influence the values of the kinetic constants for the enzyme inhibition by SA-152. This finding is consistent with the hypothesis on the irreversible binding of SA-152 in the active center of the enzyme.
     
     
147. O-alkyl-O-methylchlorformiminophenylphosphonates--effective inhibitors of neurotoxic esterases in chicken brains
     By Makhaeva G F; Kononova I V; Malygin V V; Liashenko Iu E; Sokolov V B; Martynov I V From Doklady Akademii nauk SSSR (1991), 317(4), 1009-12. Language: Russian, Database: MEDLINE
     
     
148. Effects of gamma-aminobutyric acid antagonist, 4-ethyl bicyclo-phosphate, on total and synaptic evoked responses in neurons of hippocampal slices
     By Pervukhin G Ia; Sharonova I N; Prokof'ev S E; Fedorov N B; Sokolov V B; Martynov I V From Biulleten' eksperimental'noi biologii i meditsiny (1991), 111(4), 339-41. Language: Russian, Database: MEDLINE
     Influence of 4-E-BPE on the amplitude of population spices (PS) evoked in CA1 area by Shaffer collateral stimulation in hippocampal slices were analysed. Bath application of 4-E-BPE (10(-6)-10(-5) M) led to a pronounced increase in the amplitude of the PS, the appearance of secondary PS and then introduction of GABA led to restoring original state. The 4-E-BPE was more potent than picrotoxin. These findings suggest that 4-E-BPE suppress inhibitory synaptic transmission in the CA1 region of hippocampus.
     
     
149. Inhibition of cholinesterase activity with fluorine-containing derivatives of alpha-aminophosphonic acid
     By Kuusk V V; Morozova I V; Agabekian R S; Aksinenko A Iu; Epishina T A; Sokolov V B; Kovaleva N V; Razdol'skiy A N; Fetisov V N; Martynov I V From Bioorganicheskaia khimiia (1990), 16(11), 1500-8. Language: Russian, Database: MEDLINE
     A series of O,O-diethyl-1-(N-alpha-hydrohexafluoroisobutyryl)aminoalkylphos phonates (APh) has been synthesized and their interaction with human erythrocyte acetylcholinesterase (AChE) and with horse serum butyrylcholinesterase (BuChE) studied. Most of the APhs inactivated the cholinesterases irreversible through formation of the enzyme-inhibitor intermediate. The inactivation rate constants and the enzyme-inhibitor intermediate dissociation constants are calculated. The quantitative structure-activity relationships including both hydrophobic and calculated steric parameters of substituents are developed for APh--ChE interactions. Molecular mechanics (programme MM2) was used for determining steric parameters (Es). On the basis of QSAR models analysis it was concluded that hydrophobic interactions play an essential role in APh--AChE binding, whereas for APh--BuChE binding steric interactions are essential. Presence of at least two APh binding centres on the surface of AChE and BuChE is suggested.
     
     
150. O-substituted alkylchloroformoximes as substrates and inhibitors of cholinesterases
     By Ivanov Iu Ia; Sokolov V B; Epishina T A; Martynov I V From Doklady Akademii nauk SSSR (1990), 310(5), 1253-5. Language: Russian, Database: MEDLINE
     
     
151. The effect of synthetic proteinase inhibitors of the level of human recombinant proinsulin production, secreted by a genetically engineered strain of Bacillus subtilis
     By Parfenova E V; Popov D G; Novikov A A; Sterkin V E; Strongin A Ia; Aksinenko A Iu; Korenchenko O V; Fetisov V I; Martynov I V; Sokolov V B From Bioorganicheskaia khimiia (1989), 15(7), 987-9. Language: Russian, Database: MEDLINE
     Influence of O,O,-diethyl-1-(N-alpha-hydrohexafluoroisobutyryl)amino-1- methylpropylphosphonate and O,O-diisobutyl-1-[2-(ethoxycarbonyl)aminoperfluoroprop-2-yl] -1- methylpropylphosphonate on the level of production of human proinsulin secreted by a genetically engineered culture Bacillus subtilis AJ 73 (pBINS1.0.) has been studied. The above phosphonates, being non-toxic for microorganisms, reduced degradation of proinsulin by serine proteinases.
     
     
152. Comparative study of the interaction of acetylcholinesterases of human erythrocytes and the heads of houseflies with phosphorylated alkylchloroformoximes
     By Shataeva G A; Makhaeva G F; Iankovskaia V L; Sokolov V B; Ivanov A N From Zhurnal evoliutsionnoi biokhimii i fiziologii (1988), 24(6), 791-6. Language: Russian, Database: MEDLINE
     Studies have been made on the interaction of four types of phosphorylated alkylchloroformoximes, i.e. analogues of an insecticide-acaricide valexon, with acetylcholinesterases from human erythrocytes and from the heads of the housefly Musca domestica. Antiacetylcholinesterase activity of the drugs depended both on the structure of the organophosphorus compounds, and the origin of the enzyme, indicating the existence of differences in the active surface of these acetylcholinesterases. Incorporation of one or two chloride atoms into alkylchloroformoxime group of the cleaved part of the organophosphorus compounds increased anticholinesterase activity with respect to both enzymes. Diethyl derivatives of these drugs exhibited higher specificity with respect to housefly enzyme as compared to human acetylcholinesterase.
     
     
153. Interaction of binding sites of bicyclic esters of phosphoric acids, picrotoxin and (3H)-gamma-aminobutyric acid
     By Pervukhin G Ia; Maslov A A; Kotel'nikov S A; Sokolov V B; Fetisov V I From Doklady Akademii nauk SSSR (1987), 293(3), 736-9. Language: Russian, Database: MEDLINE
     
     
154. Interaction of dialkyl(alpha-carbomethoxy-beta,beta,beta-trifluoro- ethyl) phosphates with mammalian esterases
     By Makhaeva G F; Fetisov V I; Sokolov V B; Iankovskaia V L; Goreva T V From Bioorganicheskaia khimiia (1987), 13(1), 33-7. Language: Russian, Database: MEDLINE
     The interaction of dialkyl (alpha-carbometoxy-beta,beta,beta-trifluoroethyl) phosphates (RO)2P(O) . OCH(CF3)COOMe (R = Me, Et, Pr, Pri, Bu, Bui, Am, Hex) (I-VIII) with human erythrocyte acetylcholinesterase, horse serum butyrylcholinesterase, pig liver carboxylesterase was studied and acute toxicity in mice was estimated. Compounds (I)-(VIII) were not hydrolyzed by carboxylesterase, slowly and irreversibly inhibited acetylcholinesterase (kII = 10(2)-10(4) M-1 X min-1) and more efficiently inhibited butyrylcholinesterase and carboxylesterase (kII = 10(3)-10(7) M-1 X min-1). The structure--antienzymatic activity relationships were investigated. With increasing of hydrophobicity of alkoxy groups, antienzymatic activity to butyrylcholinesterase and carboxylesterase ("sites of loss") rises equally and more significantly, than antiacetylcholinesterase activity (delta lg kII 1.0 and 2.4 for R = CH3 and C5H11 resp.). Branching at the alpha-position of alkoxy groups leads to sharp reducing of acetylcholinesterase and butyrylcholinesterase inhibition constants, the carboxylesterase inhibition mechanism becoming reversible. Multiple regression analysis (the Kubinyi model) showed that influence of steric hindrances is revealed at the phosphorylation stage. It was found that phosphates (I)-(VIII) possess low acute toxicity in mice (900-2000 mg/kg). The toxicity of this homologous series appears to be independent of the hydrophobicity. Role of esterases in toxicological effect of compounds (I)-(VIII) is discussed.
     
     

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