ABSTRACT
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.
ABSTRACT
1-(2,3-Dihydroxypropyl)-, 1-(4-hydroxy-2-oxabutyl)-, 1-(3-hydroxymethyl-4-hydroxy-2-oxabutyl)-, 1-(1,5-dihydroxy-3-oxa-2-pentyl)-, 1-(5-hydroxy-3-oxa-2-pentyl)-, and 1-(4,5-dihydroxy-2-oxapentyl)-2-trifluoromethyl- and -2-trifluoromethylthiobenzimidazoles were obtained by condensation of trimethylsilyl derivatives of 2-substituted benzimidazoles with alkylating agents in the presence of SnCl4, or by direct alkylation of the sodium salts of the heterocycles.