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1.

Вид документа : Статья из журнала
Шифр издания : 54/C 51
Автор(ы) : Kharitonova M. I., Antonov K. V., Fateev I. V., Berzina M. Ya., Kotovskaya S. K., Charushin V. N.
Заглавие : Chemoenzymatic Synthesis of Modified 2′-Deoxy-2′-fluoro-β-d-arabinofuranosyl Benzimidazoles and Evaluation of Their Activity Against Herpes Simplex Virus Type 1
Место публикации : Synthesis (Germany). - 2017. - Vol. 49, № 5. - С. 1043-1052
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): 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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2.

Вид документа : Статья из журнала
Шифр издания : 54/C 57
Автор(ы) : Chupakhin O. N., Charushin V. N., Rusinov V. L.
Заглавие : Scientific foundations for the creation of antiviral and antibacterial preparations [Электронный ресурс]
Место публикации : Herald of the Russian Academy of Sciences. - 2016. - Vol. 86, № 3. - С. 206-212
Систем. требования: http://download.springer.com/static/pdf/65/
Примечания : 26.10.16
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): triazide and azoloazine derivatives --triazavirin--protein disulfide isomerase
Аннотация: The results of the Ural scientific school's organic chemists on the creation of antiviral and antibacterial, including antitubercular, chemopreparations are considered. Basic research data were generalized on the synthesis and study of antiviral activity and the establishment of the metabolism and mechanism of azoloazine series compounds-azaanalogs of adenine and guanine, as well as their nucleosides, which led to the creation of a new family of antiviral substances. One of them, triazavirin, has become a regular therapeutic fixture as an antiflu preparation. The results of synthetic and biological studies on substituted pyrimidines, nucleosides of the benzimidazole and purine series, and other biologically active azaheterocycles are also discussed.
\\\\expert2\\NBO\\Herald of the Russian Academy of Sciences\\2016. V. 86, N 3. P. 206-212.pdf
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3.

Вид документа : Статья из журнала
Шифр издания : 54/S 98
Автор(ы) : Krasnov V. P., Vigorov A. Yu., Musiyak V. V. , Nizova I. A., Gruzdev D.A., Matveeva T. V., Levit G. L., Charushin V. N.
Заглавие : Synthesis and antimycobacterial activity of N-(2-aminopurin-6-yl) and N-(purin-6-yl) amino acids and dipeptides [Электронный ресурс]
Место публикации : Bioorganic and Medicinal Chemistry Letters. - 2016. - Vol. 26, № 11. - С. 2645-2648
Систем. требования: http://apps.webofknowledge.com/full
Примечания : 26.10.16
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): purine --glutamic acid--amino acids
Аннотация: Synthetic routes to novel N-(purin-6-yl)- and N-(2-aminopurin-6-yl) conjugates with amino acids and glycine-containing dipeptides were developed. In vitro testing of 42 new and known compounds made it possible to reveal a series of N-(purin-6-yl)- and N-(2-aminopurin-6-yl) conjugates exhibiting significant antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium avium, Mycobacterium terrae, and multidrug-resistant M. tuberculosis strain isolated from tuberculosis patients in the Ural region (Russia). N-(2-Aminopurin-6-yl)- and N-(purin-6-yl)-glycyl-(S)-glutamic acids were the most active compounds. (C) 2016 Elsevier Ltd. All rights reserved
\\\\expert2\\NBO\\Bioorganic and Medicinal Chemistry Letters\\2016, v. 26, p. 2645.pdf
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4.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Krasnov V. P., Musiyak V. V. , Levit G. L., Gruzdev D.A., Charushin V. N., Andronova V. L., Galegov G. A., Orshanskaya I. R., Sinegubova E. O., Zarubaev V. V.
Заглавие : Synthesis of pyrimidine conjugates with 4-(6-amino-hexanoyl)-7,8-difluoro-3,4-dihydro-3-methyl-2h-[1,4] benzoxazine and evaluation of their antiviral activity
Место публикации : Molecules. - 2022. - Vol. 27, № 13. - Ст.4236
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): pyrimidine
Аннотация: A series of pyrimidine conjugates containing a fragment of racemic 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine and its (S)-enantiomer attached via a 6-aminohexanoyl fragment were synthesized by the reaction of nucleophilic substitution of chlorine in various chloropyrimidines. The structures of the synthesized compounds were confirmed by 1H, 19F, and 13C NMR spectral data. Enantiomeric purity of optically active derivatives was confirmed by chiral HPLC. Antiviral evaluation of the synthesized compounds has shown that the replacement of purine with a pyrimidine fragment leads to a decrease in the anti-herpesvirus activity compared to the lead compound, purine conjugate. The studied compounds did not exhibit significant activity against influenza A (H1N1) virus.
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5.

Вид документа : Статья из журнала
Шифр издания : Г/S 98
Автор(ы) : Vozdvizhenskaya O. A., Andronova V. L., Galegov G. A., Levit G. L., Krasnov V. P., Charushin V. N.
Заглавие : Synthesis and antiherpetic activity of novel purine conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine
Место публикации : Chemistry of Heterocyclic Compounds. - 2021. - Vol. 57, № 4. - С. 490–497
ББК : Г
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): 6-chloropurine--antiviral activity--herpes simplex virus type 1
Аннотация: A method for the synthesis of novel purine conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine containing fragments of ω-amino acids with different lengths of the polymethylene chain as a linker has been developed. It was found in experiments in vitro that the obtained compounds are active against the herpes simplex virus type 1, including the acyclovir-resistant strain.
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6.

Вид документа : Статья из журнала
Шифр издания : Г/N 89
Автор(ы) : Krasnov V. P., Zarubaev V. V., Gruzdev D., Vozdvizhenskaya O., Vakarov S. A., Musiyak V. V. , Chulakov E. N., Volobueva A. S., Sinegubova E. O., Ezhikova M. A., Kodess M. I., Levit G. L., Charushin V. N.
Заглавие : Novel purine conjugates with N-heterocycles: synthesis and anti-influenza activity
Место публикации : Chemistry of Heterocyclic Compounds. - 2021. - Vol. 57, № 4. - С. 498-504
УДК : Г
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): 6-chloropurine--heterocyclic amines--antiviral activity--influenza a and b viruses
Аннотация: A number of novel amides were synthesized by coupling of 6-[(9H-purin-6-yl)amino]hexanoic acid to heterocyclic amines. The antiviral activity of the obtained compounds, as well as of purine conjugates in which 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine is linked to position 6 of purine through a fragment of ɷ-amino acids with varying lengths of polymethylene chains against influenza A and B viruses was studied in vitro. Purine derivatives have been shown to have moderate activity against influenza A (H1N1) virus. The antiinfluenza activity and cytotoxicity of conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine depend on the length of the linker fragment.
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7.

Вид документа : Статья из журнала
Шифр издания : 54/S 98
Автор(ы) : Verbitskiy E. V., Cheprakova E. M., Slepukhin P. A., Kravchenko M. A., Skornyakov S. N., Rusinov G. L., Chupakhin O. N., Charushin V. N.
Заглавие : Synthesis of novel purin-6-yl conjugates with heterocyclic amines linked via 6-aminohexanoyl fragment [Электронный ресурс]
Место публикации : Mendeleev Communications. - 2015. - Vol. 25. - С. 412-414
Систем. требования: http://www.sciencedirect.com/science/article/pii/S0959943615002011
Примечания : Bibliogr. : p. 414 (30 ref.). - 20.01.2016
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): 2-aminopurine --purin-6-yl --heterocyclic amines
Аннотация: Novel conjugates of purine and 2-aminopurine linked with heterocyclic amines, including chiral derivatives of 3,4-dihydro- 2H-[1,4]benzoxazine, 3,4-dihydro-2H-[1,4]benzothiazine and 1,2,3,4-tetrahydroquinoline, by 6-aminohexanoyl fragment at the 6-position of purine moiety were obtained. For this purpose, replacement of the chlorine atom in 2-amino-6-chloropurine or 6-chloropurine by direct nucleophilic substitution reaction with 6-aminohexanamides or the coupling of 6-(purin-6-ylamino)-6- hexanoic acid with nitrogen heterocycles were used.
\\\\expert2\\nbo\\Mendeleev Communications\\2015, v.25, p. 412.pdf
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8.

Вид документа : Статья из журнала
Шифр издания : 54/C 51
Автор(ы) : Konstantinova I. D., Selezneva O. M., Fateev I. V., Balashova T. A., Kotovskaya S. K., Baskakova Z. M., Charushin V. N., Mikhailopulo I. A.
Заглавие : Chemo-enzymatic synthesis and biological evaluation of 5,6-disubstituted benzimidazole ribo- and 2′-deoxyribonucleosides
Место публикации : Synthesis (Germany). - 2013. - Vol.45, №2, art. N SS-2012-T0784-OP. - С. 272-280
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): 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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9.

Вид документа :
Шифр издания :
Автор(ы) : Konstantinova I. D., Selezneva O. M., Kotovskaya S. K., Baskakova Z. M., Charushin V. N., Baranovsky A. V.
Заглавие : Chemo-Enzymatic Synthesis and Biological Evaluation of 5,6-Disubstituted Benzimidazole Ribo- and 2′-Deoxyribonucleosides
Место публикации : Synthesis. - 2012. - Vol.45. - С. Article in press
Ключевые слова (''Своб.индексиров.''): 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\\2012, Article in press.pdf
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10.

Вид документа : Статья из журнала
Шифр издания : 54/C 51
Автор(ы) : Eletskaya B. Z., Konstantinova I. D., Paramonov A. S., Esipov S. E., Gruzdev D.A., Vigorov A. Yu., Levit G. L., Miroshnikov A. I., Krasnov V. P., Charushin V. N.
Заглавие : Chemoenzymic arabinosylation of 2-aminopurine bearing the chiral fragment of 7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines [Электронный ресурс]
Место публикации : Mendeleev Communications. - 2016. - Vol. 26, № 1. - С. 6-8
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): purine nucleoside phosphorylase-- 2-aminopurine conjugates
Аннотация: Chemoenzymic transglycosylation of 2-​aminopurine conjugates with enantiomerically pure 7,8-​difluoro-3-​methyl-3,4-dihydro-2H-[1,4]​benzoxazines under the action of recombinant E. coli purine nucleoside phosphorylase afforded the corresponding arabinofuranosides, yields of the target compds. being dependent on both the structure and configuration of the fragment of heterocyclic amine attached at C-​6 position of purine moiety.
\\\\expert2\\nbo\\Mendeleev Communications\\2016, v.26, p. 6-8.pdf
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