SYNTHESIS OF ACYCLO C-NUCLEOSIDES: 2-(ALDITOL-1-YL)-5-ALKYLTHIO-1,3,4-THIADIAZOLINES

Abstract

Condensative cyclization of aldehydo-sugar S-methylhydrazonecarbodithioates and S-benzylhydrazonecarbodithioates with acetic anhydride in the presence of pyridine gave the corresponding 3-acetyl-2-(poly-O-acetyl-alditol-1-yl)-5-alkylthio-1,3,4-thiadiazolines. De-O-acetylation of the latter compounds gave the title acyclo C-nucleosides. The compounds prepared were found antimicrobially inactive against Escherichia coli, Bacillus subtilis, Staphylococcus aureus, and Candida albicans.

Key Words:

• aldehydo-sugar
• S-alkylhydrazonecarbodithioates
• 1,3,4-thiadiazoline acyclo C-nucleosides
• synthesis
• structure corroboration
• antimicrobial activity