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1.
Инвентарный номер: нет.
   
   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.)
ББК 54
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
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2.
Инвентарный номер: нет.
   
   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
ББК 54
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

\\\\expert2\\nbo\\Synthesis\\2013, v. 45. N 2. p. 272-280.pdf
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3.
Инвентарный номер: нет.
   
   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
ББК 54
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

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4.
Инвентарный номер: нет.
   


   
    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
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5.
Инвентарный номер: нет.
   
   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
ББК 54
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
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6.
Инвентарный номер: нет.
   
   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
ББК 54
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
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7.
Инвентарный номер: нет.
   
   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.)
ББК 54
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
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8.
Инвентарный номер: нет.
   
   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.)
ББК 54
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
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9.
Инвентарный номер: нет.
   
   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
ББК 54
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

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10.
Инвентарный номер: нет.
   
   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
ББК 54
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.

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