Design, synthesis and antimicrobial evaluation of thioglycosides of a novel class of 2-mercaptonicotinonitriles

Abstract

A new class of thioglycosides comprising a diazenyl pyridine moiety was assembled from the regioselective reaction of the acetylated α-glycopyranosyl bromide with hitherto unreported 2-mercaptonicotinonitriles. Moreover, the deacetylation of S-glycoside derivatives utilizing of methanolic ammonia solution afforded the free hydroxy thioglycosides in quantitative yields. The identity of the newly obtained derivatives has been achieved via spectroscopic and elemental analyses. All of the newly synthesized derivatives exhibited significant antimicrobial activity towards certain selected microorganisms (bacteria and fungi). Generally, S-glycoside derivatives demonstrated outstanding antibacterial and antifungal activities. Amongst them, the acetylated derivatives showed the most distinguished antifungal and antibacterial activities with a promising minimum inhibitory concentration (MIC) values in comparison with the approved drugs; Amphotericin B and Cefotaxime.

Keywords

• 2-Mercaptonicotinonitriles
• Thioglycosides
• Regioselectivity
• Antimicrobial
• MIC