Thiosugar nucleosides. Synthesis and biological activity of 1,3,4-thiadiazole, thiazoline and thiourea derivatives of 5-thio-D-glucose.

New acylated 5-thio-beta-D-glucopyranosylimino-disusbstituted 1,3,4-thiadiazols 8, and 11 were prepared, via spontaneous rearrangements, by cycloaddition of the glycosyl isothiocyanate 2 with the reactive intermediates 1-aza-2-azoniaallene hexachloroantimonates 4 and 6, respectively. Reaction of 2 with aminoacetone or chloroethylamine afforded the acylated 5-thio-beta-D-glucopyranosyl-4-imidazoline-2-thione nucleoside 16 and glucopyranosylamino-2-thiazoline derivative 18, respectively. Deblocking of 8, 11, 17 and 19 furnished the free nucleoside analogues 9, 12, 18 and 20, respectively. Analogously, treatment of 2 with chloroethylamine in the 1:2 ratio afforded the thioureylendisaccharide 21. No in vitro antiviral activity against HIV-1, HIV-2, human cytomegallovirus (HMCV), has been found for the new synthesized compounds.