SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF ISOXAZOLYL AZETIDIN-2-ONES AND THIAZOLIDIN-4-ONES

摘要

A series of novel isoxazolyl azetidin-2-ones, 4a-h and thiazolidin-4-ones, 5a-h were synthesized from (E)-3- (methylimino)-N-(5-methylisoxazol-3-yl)butanamides, 3a-h. The four-membered β-lactam ring was built by adding choloroacetyl chloride to butanamides, 3a-h in the presence of triethylamine to give 4a-h. Cyclocondensation of mercapto acetic acid with, 3a-h in presence of anhydrous ZnCl2 resulted in the formation of thiazolidin-4-ones, 5ah. The newly synthesized compounds, 4a-h and 5a-h were confirmed using IR, 1HNMR, 13CNMR and mass spectral data and were evaluated for in vitro antibacterial activity. From the results, it is evident that the compounds 4d and 5d are showing exceptional antibacterial activity. Insilico ADME studies were performed and the results highlighted the designed compounds are safe to be considered as drug like molecules.