П 50 Полифторбензоилхлориды и изотиоцианаты в реакциях с СH-активными бензимидазолами [] = Polyfluorobenzoyl chlorides and isothiocyanates in reactions with CH-reactive benzimidazoles / Э. В. Носова, Г. Н. Липунова, А. А. Лаева, В. Н. Чарушин // Изв. АН. Сер. Химическая. - 2005. - N 3. - 720-724: рис. - Библиогр. : с. 724 (24 назв.) . - ISSN 0002-3353 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Взаимодействием (2-бензоилметил)бензимидазола с тетра- и пентафторбензоилхлоридами получены фторсодержащие 6-бензоил-7H-бензимидазо[3,2-а]хинолоны. На основе 2-цианометилбензимидазола или 2-бензоилметилбензимидазола и тетра(пента)фторбензоилизотиоцианатов синтезированы фторсодержащие 1,3-бензотиазиноны, для которых выявлены различия в реакциях с циклоалкилиминами. |
С 38 Синтез и противовирусная активность фторсодержащих производных пиридо[1,2-а]бензимидазолов [] = Synthesis and antiviral activity of fluorinated pyrido[1,2-a]benzimidazoles / С. К. Котовская, З. М. Баскакова, В. Н. Чарушин, О. Н. Чупахин // Химико-фармацевтический журнал. - 2005. - Т. 39, N 11. - 12-16: табл. - Библиогр. : с. 16 (16 назв.) . - ISSN 0023-1134 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Разработаны методы синтеза фторсодержащих производных пиридо[1,2-а]бензимидазолов,предназначенных для биологического тестирования. Реакцией 1,2-диамино-4,5-дифторбензола (I) с цианоуксусным эфиром впервые синтезирован 5,6-дифтор-2-циано-бензимидазол(II), конденсацией которого с эфирами этоксиметиленмалоновой кислоты и ацетоуксусным эфиром получены пиридо[1,2]бензимидазолы (III, IV). Пиридо[1,2-а]бензимидазолы (III-XIII) были подвергнуты скринингу на противовирусную и цитотоксическую активность в Государственном научном центре вирусологии и биотехнологии "Вектор" на культуре клеток Vero в отношении ортопксивирусов, патогенных для человека |
S 98 Synthesis and antiviral activity of fluorinated pyrido[1,2-a]benzimidazoles [Electronic resource] / S. K. Kotovskaya, Z. M. Baskakova, V. N. Charushin, O. N. Chupakhin, E. F. Belanov, N. I. Bormotov, S. M. Balakhnin, O. A. Serova // Pharmaceutical Chemistry Journal. - 2005. - Vol. 39, № 11. - P574-578. - Библиогр. : с. 578 (16 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- ANTIVIRAL ACTIVITY Аннотация: Methods for the synthesis of fluorinated pyrido[1,2-a]benzimidazoles have been developed, and a series of such compounds has been obtained and studied for biological activity. In particular, 5,6-difluoro-2-cyanobenzimidazole (II) was synthesized for the first time using the reaction of 1,2-diamino-4,5-difluorobenzole (I) with cyanoacetic ether. Pyrido[1,2-a]benzimidazoles (III, IV) were obtained via condensation of benzimidazole II with diethylethoxymethylene malonate and ethyl acetoacetate. The synthesized pyrido[1,2-a]benzimidazoles (III–XIII) were subjected to screening on a culture of Vero cells for antiviral activity and cytotoxicity with respect to ortho-poxviruses that are pathogenic for humans. ?? \\\\Expert2\\nbo\\Pharmaceutical Chemistry Journal\\2005, 39 (11),574.pdf |
S 98 Synthesis of 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-1,4-benzoxazines from oxides of internal perfluoroolefins [Electronic resource] / L. V. Saloutina, A. Ya. Zapevalov, V. I. Saloutin, M. I. Kodess, V. E. Kirichenko, M. G. Pervova, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2005. - Vol. 126, № 6. - P976-983 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of oxides of internal trans-, cis-perfluoroolefins with o-phenylenediamine and 2-aminophenol in dioxane gave 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-2H-1,4-benzoxazin-2-ols respectively in yields of 23–67%. When N,N-dimethylacetamide was used as a solvent an anionic isomerization of the oxides into ketones, which further yielded 2-(perfluoroalkyl)benzimidazoles in the case of o-phenylenediamine and 2-hydroxy-N-perfluoroalkanoylanilines in the case of 2-aminophenol, became the main path of these reactions. Unusual cyclization resulting in 2-pentafluoroethyl-2-pentafluoropropanoylbenzoxazolidine occurs on interaction between dodecafluoro-3,4-epoxyhexane and 2-aminophenol in N,N-dimethylacetamide. \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2005, v.126, p.976.pdf |
M 61 Metal and boron derivatives of fluorinated cyclic 1,3-dicarbonyl compounds [Text] / D. V. Sevenard, O. G. Khomutov, N. S. Boltacheva, V. I. Filyakova, V. Vogel, V. Ya. Sosnovskikh, V. O. Iaroshenko, G. -V. Roeschenthaler // Zeitschrift fur Naturforschung - Section B. Journal of Chemical Science. - 2009. - Vol. 64, № 5. - P541-550 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Starting from the corresponding cyclic 1,3-diketones or other precursors (cyclic ketones as well as lactones), several new salts and chelate complexes of fluorinated 1,3-dicarbonyls were obtained. Their preparative significance was demonstrated by straightforward syntheses of fluorinated pyrazoles, benzimidazoles and 1,7-ketoesters. The structure of a boron chelate of 2-(trifluoroacetyl)- cyclohexanone was investigated by X-ray diffraction |
P 80 Polyfluorobenzoyl chlorides and isothiocyanates in reactions with CH-reactive benzimidazoles [Electronic resource] / E. V. Nosova, G. N. Lipunova, A. A. Laeva, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2005. - Vol. 54, № 3. - P733-737 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of 2-benzoylmethylbenzimidazole with tetra- and pentafluorobenzoyl chlorides afford fluorine-containing 6-benzoyl-7H-benzimidazo[3,2-a]quinolones. 2-Cyanomethyl- or 2-benzoylmethylbenzimidazole reacts with tetra(penta) fluorobenzoyl isothiocyanates to give fluorine containing 1,3-benzothiazinones, which differently behave in reactions with cycloalkylimines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2005, 54 (3), 733.pdf |
S 98 Synthesis and reactivity of monothiooxamides of the aminonitroarene series [Electronic resource] / V. N. Yarovenko, A. V. Polushina, K. S. Levchenko, I. V. Zavarzin, M. M. Krayushkin, S. K. Kotovskaya, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 6. - P1276-1280 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Monothiooxamides containing aminonitrobenzene and aminonitropyridine fragments have been synthesized. A possibility to synthesize thioesters and fused imidazole and diazepine derivatives on their basis has been demonstrated \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (6), 1276-1280.pdf |
R 30 Reactions of fluoroalkyl-containing lithium 1,3-diketonates with diaminoarenes and 2-aminobenzenethiol [Electronic resource] / V. I. Filyakova, N. S. Boltacheva, D. V. Sevenard, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2010. - Vol. 59, № 9. - P1791-1796. - Bibliogr. : p. 1796 (25 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): FLUOROALKYL -- CONTAINING LITHIUM 1,3-DIKETONATES -- 1,2-DIAMINOBENZENE -- 2,3-DIAMINONAPHTHALENE -- 1,2-DIAMINO-4,5-DIFLUOROBENZENE -- 2-AMINOBENZENETHIOL Аннотация: 1,5-Benzo[b]- and 1,5-naphtho[2,3-b]diazepines were synthesized by the reaction of lithium 1,3-diketonates with 1,2-diaminobenzene and 2,3-diaminonaphthalene in an MeOH-AcOH-HCl mixture at 0 °C. The reactions of fluoroalkyl-containing lithium 1,3-diketonates with 1,2-diaminobenzene and 1,2-diamino-4,5-difluorobenzene under reflux in acetic acid afford 2-fluoroalkyl-containing benzimidazoles as the major products, whereas the reaction with 2-aminothiophenol gives 2-phenylbenzothiazole. The reactions of lithium diketonate containing the cyclohexane and cyclopentane moieties with 1,2-diaminoarenes and 2-aminobenzenethiol are accompanied by the opening of the carbocycle to form 2-(6-oxo-7,7,7-trifluoroheptyl)benzimidazole and 2-(5-oxo-6,6,6-trifluorohexyl)benzothiazole hydrates, respectively. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2010, 59 (9), 1791-1796.pdf |
G 65 Goryaeva, M. V. Synthesis of pyrimido[1,2-alfa]benzimidazoles from ethyl 2-ethoxymethylidene-3-oxo-3-(polyfluoroalkyl)propionates [Electronic resource] / M. V. Goryaeva, Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2010. - Vol. 46, № 3. - P432-438 : рис., табл. - Bibliogr. : p. 438 (22 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BENZIMIDAZOLES -- ETHYL -- PROPIONATES Аннотация: Cyclization of ethyl 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates with benzimidazol-2-amine in boiling 1,4-dioxane followed two concurrent pathways with participation of fluoroacyl and ethoxycarbonyl fragments and formation of, respectively, ethyl 4-hydroxy-4-polyfluoroalkyl-1,4-dihydropyrimido-[1,2-alfa]benzimidazole-3-carboxylates and 3-polyfluoroacylpyrimido[1,2-alfa]benzimidazol-4-ols. Dihydropyrimido[1,2-alfabenzimidazole derivatives undergo dehydration to give ethyl 4-(polyfluoroalkyl)pyrimido[1,2-alfa]benzimidazole-3-carboxylates, whereas the hydroxy group in 3-polyfluoroacylpyrimido[1,2-a]benzimidazol-4-ols is capable of being replaced by the amino group of the second benzimidazole molecule with formation of 4-(1H-benzimidazol-2-ylamino)-3-polyfluoroacylpyrimido[1,2-alfa]benzimidazoles. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2010, 46 (3), 432-438.pdf |
Chemo-Enzymatic Synthesis and Biological Evaluation of 5,6-Disubstituted Benzimidazole Ribo- and 2′-Deoxyribonucleosides / I. D. Konstantinova, O. M. Selezneva, S. K. Kotovskaya, Z. M. Baskakova, V. N. Charushin, A. V. Baranovsky // Synthesis. - 2013. - Vol.45, № 2. - С. 272-280 Кл.слова (ненормированные): 5,6-DISUBSTITUTED BENZIMIDAZOLES -- NUCLEOSIDES -- PURINE NUCLEOSIDE PHOSPHORYLASE Аннотация: A number of new 5,6-disubstituted benzimidazoles have been prepared and their substrate properties for recombinant E. coli purine nucleoside phosphorylase (PNP; the product of the deoD gene) in the transglycosylation reaction were investigated. The heterocyclic- bases showed good substrate activity for PNP and the ribo- and 2′-deoxyribonucleosides were synthesized. The predominant (OMe and OEt) or exclusive (Oi-Pr, morpholino, and N-methylpiperazino) formation of the 5-substituted 6-fluoro-1-(β-D-ribofuranosyl)benzimidazoles was observed. The formation of the regioisomeric 6- methoxy-, 6-ethoxy-, or 6-isopropoxy-substituted 1-(2-deoxy-β-D-ribofuranosyl)-5-fluorobenzimidazoles was observed in the trans-2-deoxyribosylation reaction of the corresponding bases. The predominant or exclusive formation of the regioisomeric N1-nucleosides with bulky 5-substituents of 6-fluorobenzimidazole points to a large hydrophobic pocket in the E. coli PNP active site that can accommodate these groups. The biological activity of the synthesized nucleosides was studied and revealed no inhibitory activity against a broad variety of DNA and RNA viruses. The compounds also lacked significant cy \\\\expert2\\nbo\\Synthesis\\2013, v. 45. N 2. p. 272-280.pdf |
R 35 Regiodirected synthesis of polyfluoro-alkylated pyrimido[1,2-a]benzimidazoles / M. V. Goryaeva, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 2012. - Vol.48, №2. - С. 372-376 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- BENZIMIDAZOLES -- CYCLIZATION Аннотация: Conditions have been found for the regiodirected cyclization of 2-aminobenzimidazoles using ethyl 3-oxo-3-polyfluoroalkyl-2-ethoxymethylidenepropionates at the ethoxymethylidenefluoroacyl fragment to give ethyl pyrimidobenzimidazole-3-carboxylates \\\\Expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2012, v.48, N 2, p.372-376.pdf |
F 70 Fluorinated derivatives of benz[4,5]imidazo[2,1-b][1,3]thiazoles are inhibitors of measles viruses [Электронный ресурс] / A. G. Pokrovskii, E. A. Il"ichyova, S. K. Kotovskaya, S. A. Romanova, V. N. Charushin, O. N. Chupakhin // Doklady Akademii Nauk . - 2004. - Vol.398, №3. - P412-414 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ANTIVIRAL ACTIVITY -- CYTOTOXICITY -- FLUORINATED BENZIMIDAZOLES Аннотация: The results of in vitro anti-virus activity investigation for the new benzimidazoles (their synthesis is reported previously) are presented. The activity of the most active compound was studied in dependence of its introduction to the culture (before virus adsorption, simultaneously with virus, directly after virus adsorption, after 6 hours and after 1 day). Preliminary treatment of cells didn't protect them from further infecting; therewith the compound introduction simultaneously with virus or after infection caused no considerable effect on its anti-virus activity. The latter is attributed to blocking of late stages of measles virus reproduction - synthesis or arrangement of virus proteins |
C 51 Chemo-enzymatic synthesis and biological evaluation of 5,6-disubstituted benzimidazole ribo- and 2′-deoxyribonucleosides [Электронный ресурс] / I. D. Konstantinova, O. M. Selezneva, I. V. Fateev, T. A. Balashova, S. K. Kotovskaya, Z. M. Baskakova, V. N. Charushin, I. A. Mikhailopulo // Synthesis (Germany). - 2013. - Vol.45, №2, art. N SS-2012-T0784-OP. - P272-280 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 5,6-DISUBSTITUTED BENZIMIDAZOLES -- NUCLEOSIDES -- SUBSTRATE PROPERTIES Аннотация: A number of new 5,6-disubstituted benzimidazoles have been prepared and their substrate properties for recombinant E. coli purine nucleoside phosphorylase (PNP; the product of the deoD gene) in the transglycosylation reaction were investigated. The heterocyclic bases showed good substrate activity for PNP and the ribo- and 2-deoxyribonucleosides were synthesized. The predominant (OMe and OEt) or exclusive (Oi-Pr, morpholino, and N-methylpiperazino) formation of the 5-substituted 6-fluoro-1-(β-d- ribofuranosyl)benzimidazoles was observed. The formation of the regioisomeric 6- methoxy-, 6-ethoxy-, or 6-isopropoxy-substituted 1-(2-deoxy-β-d- ribofuranosyl)-5-fluorobenzimidazoles was observed in the trans-2- deoxyribosylation reaction of the corresponding bases. The predominant or exclusive formation of the regioisomeric N1-nucleosides with bulky 5-substituents of 6-fluorobenzimidazole points to a large hydrophobic pocket in the E. coli PNP active site that can accommodate these groups. The biological activity of the synthesized nucleosides was studied and revealed no inhibitory activity against a broad variety of DNA and RNA viruses. The compounds also lacked significant cytotoxicity |
S 89 Structure of substituted 2-(phenoxy)benzimidazoles [Electronic resource] / I. S Pavlova, I. G. Pervova, G. N. Lipunova, R. K. Novikova, P. A. Slepukhin, I. N. Lipunov // Crystallography Reports. - 2013. - Vol.58, №2. - С. 271-274. - Bibliogr. : p. 274 (7 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ARYL FRAGMENTS -- AZO-HYDRAZONE -- BENZIMIDAZOLES Аннотация: The synthesis and X-ray diffraction study of 1-benzyl-2-[2-(5- ethyltetrazole-2-yl)-phenoxy]-1H-benzimidazole and 1-benzyl-2-[2-(5- ethyltetrazole-2-yl)-4-nitrophenoxy]-1H-benzimidazole single crystals have been performed. The oxidative splitting of an azo-hydrazone group of 1-(2-hydroxy-(5-nitro)phenyl)-3-ethyl-5-(benzylbenzimidazolyl)formazans, a break in the C2-N1 bond, the interaction of o-hydroxyl group of aryl fragment with oxygen, and the formation of new 2-(phenoxy)benzimidazoles are found to occur in the presence of perchlorate iron(III). \\\\expert2\\nbo\\Crystallography Reports (Кристаллография)\\2013, v.58, N 2, p.271-274.pdf |
L 79 Lipunova, G. N. Fluorine-Containing Benzimidazoles and Their [a ]- and [b ]Heteroannelated Derivatives: Synthesis and Biological Activity (Review) [Electronic resource] / G. N. Lipunova, E. V. Nosova, V. N. Charushin // Chemistry of Heterocyclic Compounds. - 2014. - Vol. 50, № 6. - С. 764-790. - Bibliogr. : p. 789-790 (79 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BENZIMIDAZOLES -- FLUORINE-CONTAINING BENZIMIDAZOLES Аннотация: Published data from 1992-2013 on methods for the synthesis and biological activity of fluorine-containing benzimidazoles and their [a]- and [b]heteroannelated derivatives are summarized and classified \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2014, v.50, N 6, p. 764-790.pdf |
C 51 Chemoenzymatic Synthesis and Antiherpes Activity of 5-Substituted 4,6-Difluorobenzimidazoles Ribo- and 2′-Deoxyribonucleosides [Электронный ресурс] / M. I. Kharitonova, I. V. Fateev, A. L. Kayushin, I. D. Konstantinova, S. K. Kotovskaya, V. L. Andropova, G. A. Galegov, V. N. Charushin, A. I. Miroshnikov // Synthesis (Germany). - 2016. - Vol. 48, № 3. - С. 394-406. - Bibliogr. : p. 405-406 (37 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): DRUG DISCOVERY- -- NUCLEOSIDES -- HERPES SIMPLEX VIRUS Аннотация: A series of 5,6-disubstituted benzimidazole nucleosides, obtained earlier, did not show any significant antiviral activity at relatively low cytotoxicity in vitro. In the course of our research we have succeeded in introducing an additional fluorine atom into the benzimidazole ring system. A new series of 4,6-difluorobenzimidazoles, bearing various groups (fluoro-, methoxy-, ethoxy-, morpholino-, and pyrrolidino-) in the 5-position of the benzene ring, have been synthesized. All these compounds proved to be substrates for recombinant E. coli purine nucleoside phosphorylase (PNP) in the transglycosylation reaction. Effective methods for the synthesis of ribo- and 2′-deoxyribonucleosides with high yields (60–90%) have been described, and the formation of regioisomeric N3-nucleosides of benzimidazoles have been detected. The biological activity of the nucleosides obtained against herpes simplex virus type 1 (HSV-1) has been elucidated. All compounds show a low cytotoxicity in the cell culture Vero E6. 4,5,6-Trifluoro-1-(β-d-ribofuranosyl)benzimidazole and 5-methoxy-4,6-difluoro-1-(β-d-2′-deoxyribofuranosyl)benzimidazole proved to inhibit completely the progression of the virus cytopathic effect (CPE) at a multiplicity of infection (MOI) of 0.01 PFU/cell. \\\\expert2\\nbo\\Synthesis\\2016, v. 48. p.394-406.pdf |
C 51 Chemoenzymatic Synthesis of Modified 2′-Deoxy-2′-fluoro-β-d-arabinofuranosyl Benzimidazoles and Evaluation of Their Activity Against Herpes Simplex Virus Type 1 / M. I. Kharitonova, K. V. Antonov, I. V. Fateev, M. Ya. Berzina, S. K. Kotovskaya, V. N. Charushin // Synthesis (Germany). - 2017. - Vol. 49, № 5. - С. 1043-1052 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHEMOENZYMATIC SYNTHESIS -- BENZIMIDAZOLES -- HERPES SIMPLEX VIRUS TYPE 1 Аннотация: 1-(2′-Deoxy-2′-fluoro-β-d-arabinofuranosyl)benzimidazoles containing 4,6-difluoro-, 4,5,6-trifluoro-, 5-fluoro-6-methoxy-, and 5-methoxy-4,6-difluorobenzimidazole fragments were synthesized by using purine nucleoside phosphorylase-catalyzed chemoenzymatic approach. As expected, enzymatic synthesis of nucleosides proceeds in lower yields of target compounds in comparison with the synthesis of ribo- and 2′-deoxyribobenzimidazoles (40–55% vs 60–90%). The compounds obtained were tested against the herpes simplex virus type 1, by using the Vero E6 cells. 5-Methoxy-4,6-difluoro-1-β-d-(2′-deoxy-2′-fluoroarabinofuranosyl)benzimidazole did not show any antiviral activity, when used in nontoxic concentration. All other nucleosides proved to exhibit a selective antiherpes activity. In contrast, it was shown that benzimidazole-β-d-arabinofuranosides of both di- and trisubstituted derivatives, having substituents in positions 4–6 of the benzene ring, as well as unsubstituted compounds, cannot be synthesized by enzymatic transglycosylation. 1-(β-d-Arabinofuranosyl)benzimidazole was obtained through glycosylation of N-trimethylsilylbenzimidazole with 1-chloro-2,3,5-O-methoxymethyl-d-arabinose. The behavior of this compound, as inhibitor of purine nucleoside phosphorylase (PNP) E. сoli, was investigated. 1-(β-d-Arabinofuranosyl)benzimidazole was found to belong to a mixed type of inhibitors of PNP. This fact explains why all attempts to perform enzymatic arabinosylation of 4,6-di-, 5,6-di-, and 4,5,6-trisubstituted benzimidazoles failed \\\\expert2\\NBO\\Synthesis\\2017, v. 49(5), p. 1043-1052.pdf |
N 52 New modified 2-aminobenzimidazole nucleosides: Synthesis and evaluation of their activity against herpes simplex virus type 1 / M. I. Kharitonova, A. O. Denisova, A. L. Kayushin, I. D. Konstantinova, A. I. Miroshnikov, S. K. Kotovskaya, V. N. Charushin, V. L. Andronova, G. A. Galegov // Bioorganic and Medicinal Chemistry Letters. - 2017. - Vol. 27, № 11. - P2484-2487 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ANTIVIRAL ACTIVITY -- BENZIMIDAZOLES -- FLUORINATED COMPOUNDS -- NUCLEOSIDE PHOSPHORYLASES -- NUCLEOSIDES -- TRANSGLYCOSYLATION REACTION Аннотация: Using the enzymatic transglycosylation reaction β-d-ribo- and 2′-deoxyribofuranosides of 2-amino-5,6-difluorobenzimidazole nucleosides have been synthesized. 2-Amino-5,6-difluoro-benzimidazole riboside proved to exhibit a selective antiviral activity (selectivity index >32) against a wild strain of the herpes simplex virus type 1, as well as towards virus strains that are resistant to acyclovir, cidofovir, and foscarnet. We believe that this compound might be used for treatment of herpes infections in those cases, when acyclovir is not efficient. \\\\Expert2\\NBO\\Bioorganic and Medicinal Chemistry Letters\\2017 v.27 p.2484-2487.pdf |
P 99 Pyrimido[1,2-a]benzimidazoles: synthesis and perspective of their pharmacological use / V. V. Fedotov, V. L. Rusinov, E. N. Ulomsky [et al.] // Chemistry of Heterocyclic Compounds. - 2021. - Vol. 57, № 4. - P383–409 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 2-AMINOBENZIMIDAZOLE -- PYRIMIDO[1,2-A]BENZIMIDAZOLES -- POLYNITROGEN-CONTAINING HETEROARENES -- HETEROCYCLIZATION -- MULTICOMPONENT REACTIONS Аннотация: The review presents data on the synthesis as well as studies of biological activity of new derivatives of pyrimido[1,2-a]benzimidazoles published over the last decade. The bibliography of the review includes 136 sources. |
Synthesis, fungicidal activity, and molecular docking of 2-acylamino and 2-thioacylamino derivatives of 1 H-benzo[ d]imidazoles as anti-tubulin agents / K. L. Obydennov, T. A. Kalinina, N. A. Galieva [et al.] // Journal of agricultural and food chemistry. - 2021. - Vol. 69, № 40. - P12048-12062 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BENZIMIDAZOLES -- ANTIFUNGAL ACTIVITY -- TUBULIN -- CARBENDAZIM Аннотация: This work deals with the synthesis and evaluation of fungicidal activity of benzimidazole derivatives, which are structural analogues of commercial anti-tubulin fungicides. A number of N-acyl and N-thioacyl derivatives of 2-amino-1H-benzo[d]imidazole were prepared, and their fungicidal activity against 13 strains of phytopathogenic fungi was studied. The most active compounds against the majority of the studied strains were 3a, 4l, and 4o, and the EC50 values of these compounds were in the range 2.5–20 μg/mL. Compound 3a showed the highest activity against the P. infestans strain, the growth of which is not suppressed by carbendazim. The formation of ligand–receptor complexes of various tautomeric forms of the studied benzimidazoles with homologous models of β-tubulins of B. cinerea, F. oxysporum, and P. infestans was modeled. Induced fit docking has been used for the simulation. The obtained data suggest the possibility of binding of benzimidazole fungicides to β-tubulin in the ″nocodazole cavity″ in the tautomeric form bearing a double exocyclic C═N bond. The importance of the formation of hydrogen bonds of benzimidazoles with the amino acid residue Val236 along with the Glu198 residue is also revealed in the present study. |