Synthesis, Identification, and Antibacterial Activity of Thioglycoside Derivatives of 1,3,4-Oxadiazole-2-thiols

Abstract

Thioglycoside analogues play an important role in different pharmaceutical products; therefore, we synthesized new thioglycoside analogues containing a 2-sulfanyl-1,3,4-oxadiazole moiety. The main steps of the synthesis were condensation of benzohydrazides with carbon disulfide to form 5-aryl-1,3,4-oxadiazole-2-thiols which were coupled with bromo sugars in the presence of triethylamine to afford the corresponding S-glycoside analogues. The subsequent deprotection of the latter in basic medium gave free thioglycoside derivatives. The structure of all isolated compounds was confirmed by FT-IR and ¹H and ¹³C NMR spectroscopy. The target products showed good antibacterial activity in vitro.