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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

Ramzan, M.Shahid.; Abbasi, M.Athar.; Rehman, A.; Siddiqui, S.Zahra.; Shah, S.Adnan.Ali.; Ashraf, M.; Mirza, B.; Ismail, H.

Pakistan Journal of Pharmaceutical Sciences 31(3(Supplementary): 1051-1059

2018

ISSN/ISBN: 1011-601X
PMID: 29731443
Document Number: 695496
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, 1H-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.

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