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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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Detalles Bibliográficos
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
Descripción
Sumario: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.