SYNTHESIS OF ACYCLO-C-NUCLEOSIDES - 2-(ALDITOL-1-YL)-5-METHYLTHIO-1,3,4-THIADIAZOLE AND 2-(ALDITOL-1-YL)-5-BENZYLTHIO-1,3,4-THIADIAZOLE

Condensation of S-methylhydrazinecarbodithioate or S-benzylhydrazineca rbodithioate with aldopentoses or aldohexoses gave the corresponding a ldehydo-sugar S-methylhydrazonecarbodithioates of S-benzylhydrazonecar bodithioates. Oxidative cyclization of these hydrazones with bromine i n acetic acid gave the corresponding 2-(alditol-1-yl)-5-alkylthio-1,3, 4-thiadiazoles. Acetylation of the latter gave the corresponding per-O -acetyl derivatives which were also obtained by one-pot preparation by treatment of the hydrazones with bromine and sodium acetate in acetic acid followed by acetic anhydride. Some of the prepared compounds wer e tested for antimicrobial activity against Eschericha coli, Bacillus subtilis, Staphylococcus aureus and Candida albicans. While hydrazones showed significant activity against these organisms, the thiadiazoles were devoid of antimicrobial activity.