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Acyclic analogs of nucleosides. Synthesis and in vitro antiviral activity of hydroxyalkyl-2-(trifluoromethylthiomethyl) benzimidazoles

In a search for novel antiviral compounds of the ‘doubly modified’ nucleoside type, we have prepared 1-(4-hydroxy-2-oxabutyl)-, 1-(4-hydroxy-3-hydroxymethyl-2-oxabutyl)-, 1-(4-hydroxy-1-hydroxymethy1-2-oxabutyl)-, 1-(4-hydroxy-1-methyl-2-oxabutyl), 1-(4,5-dihydroxy-2-oxapentyl)-, 1-(5-hydroxy-2-oxap...

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Autores principales: Yavorskii, A. é., Turov, A. V., Gogoman, I. V., Sobko, A. I., Tatskaya, V. N., Kvachev, V. G., Florent'ev, V. L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Kluwer Academic Publishers-Plenum Publishers 1989
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7087781/
https://www.ncbi.nlm.nih.gov/pubmed/32214415
http://dx.doi.org/10.1007/BF00480754
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author Yavorskii, A. é.
Turov, A. V.
Gogoman, I. V.
Sobko, A. I.
Tatskaya, V. N.
Kvachev, V. G.
Florent'ev, V. L.
author_facet Yavorskii, A. é.
Turov, A. V.
Gogoman, I. V.
Sobko, A. I.
Tatskaya, V. N.
Kvachev, V. G.
Florent'ev, V. L.
author_sort Yavorskii, A. é.
collection PubMed
description In a search for novel antiviral compounds of the ‘doubly modified’ nucleoside type, we have prepared 1-(4-hydroxy-2-oxabutyl)-, 1-(4-hydroxy-3-hydroxymethyl-2-oxabutyl)-, 1-(4-hydroxy-1-hydroxymethy1-2-oxabutyl)-, 1-(4-hydroxy-1-methyl-2-oxabutyl), 1-(4,5-dihydroxy-2-oxapentyl)-, 1-(5-hydroxy-2-oxapentyl), 1-(5-hydroxy-1-chloromethyl-2-oxapentyl)-, and 1-(6-hydroxy-1-chloromethyl-2-oxahexyl)-2-(trifluoromethylthiomethyl)benzimidazole. They were obtained by condensing the trimethylsilyl derivative of 2-(trifluoromethylthiomethyl) benzimidazole with alkylating agents in the presence of an equimolar mixture of trifluoromethanesulfonic acid and trimethylchlorosilane. These nucleoside analogs showed moderate antiviral activity against some RNA viruses.
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spelling pubmed-70877812020-03-23 Acyclic analogs of nucleosides. Synthesis and in vitro antiviral activity of hydroxyalkyl-2-(trifluoromethylthiomethyl) benzimidazoles Yavorskii, A. é. Turov, A. V. Gogoman, I. V. Sobko, A. I. Tatskaya, V. N. Kvachev, V. G. Florent'ev, V. L. Chem Heterocycl Compd (N Y) Article In a search for novel antiviral compounds of the ‘doubly modified’ nucleoside type, we have prepared 1-(4-hydroxy-2-oxabutyl)-, 1-(4-hydroxy-3-hydroxymethyl-2-oxabutyl)-, 1-(4-hydroxy-1-hydroxymethy1-2-oxabutyl)-, 1-(4-hydroxy-1-methyl-2-oxabutyl), 1-(4,5-dihydroxy-2-oxapentyl)-, 1-(5-hydroxy-2-oxapentyl), 1-(5-hydroxy-1-chloromethyl-2-oxapentyl)-, and 1-(6-hydroxy-1-chloromethyl-2-oxahexyl)-2-(trifluoromethylthiomethyl)benzimidazole. They were obtained by condensing the trimethylsilyl derivative of 2-(trifluoromethylthiomethyl) benzimidazole with alkylating agents in the presence of an equimolar mixture of trifluoromethanesulfonic acid and trimethylchlorosilane. These nucleoside analogs showed moderate antiviral activity against some RNA viruses. Kluwer Academic Publishers-Plenum Publishers 1989 /pmc/articles/PMC7087781/ /pubmed/32214415 http://dx.doi.org/10.1007/BF00480754 Text en © Plenum Publishing Corporation 1989 This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic.
spellingShingle Article
Yavorskii, A. é.
Turov, A. V.
Gogoman, I. V.
Sobko, A. I.
Tatskaya, V. N.
Kvachev, V. G.
Florent'ev, V. L.
Acyclic analogs of nucleosides. Synthesis and in vitro antiviral activity of hydroxyalkyl-2-(trifluoromethylthiomethyl) benzimidazoles
title Acyclic analogs of nucleosides. Synthesis and in vitro antiviral activity of hydroxyalkyl-2-(trifluoromethylthiomethyl) benzimidazoles
title_full Acyclic analogs of nucleosides. Synthesis and in vitro antiviral activity of hydroxyalkyl-2-(trifluoromethylthiomethyl) benzimidazoles
title_fullStr Acyclic analogs of nucleosides. Synthesis and in vitro antiviral activity of hydroxyalkyl-2-(trifluoromethylthiomethyl) benzimidazoles
title_full_unstemmed Acyclic analogs of nucleosides. Synthesis and in vitro antiviral activity of hydroxyalkyl-2-(trifluoromethylthiomethyl) benzimidazoles
title_short Acyclic analogs of nucleosides. Synthesis and in vitro antiviral activity of hydroxyalkyl-2-(trifluoromethylthiomethyl) benzimidazoles
title_sort acyclic analogs of nucleosides. synthesis and in vitro antiviral activity of hydroxyalkyl-2-(trifluoromethylthiomethyl) benzimidazoles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7087781/
https://www.ncbi.nlm.nih.gov/pubmed/32214415
http://dx.doi.org/10.1007/BF00480754
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