2-{[5-(Substituted-phenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(1,3- thiazol-2-yl)acetamides: New bi-heterocycles as possible therapeutic agents

Abstract

An electrophile, N-(1,3-thiazol-2-yl)-2-bromoacetamide (3), was synthesized by the reaction of 1,3-thiazole-2- amine (1) and 2-bromoethanoyl bromide (2) in an aqueous medium. A series of carboxylic acids, 7a-j, were converted into 1,3,4-oxadiazole heterocyclic core, through a series of three steps. The final compounds, 8a-j, were synthesized by stirring 7a-j and 3 in an aprotic polar solvent. The structural elucidation of the synthesized compounds was supported by IR, EI-MS, 1 H-NMR, and 13C-NMR spectral data. Title compounds were evaluated for enzyme inhibition against cholinesterases and α-glucosidase enzymes and their cytotoxic behavior was monitored using brine shrimp assay. The enzyme inhibitor potential of compounds was supported by molecular docking studies.