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 alpha-glucosidase enzymes and their cytotoxic behavior was monitored using brine shrimp assay. The enzyme inhibitor potential of compounds was supported by molecular docking studies