A series of novel thiazolidinediones were prepared by incorporating pharmacologically significant moieties viz. ester, hydrazide and substituted amine groups linked to the central phenyl ring as well as replacement of phenyl by heterocycle like substituted furan ring by employing multistep synthetic protocols. The structures of the newly synthesized target molecules were established by spectral data. The synthesized compounds were tested for their in vitro antibacterial activity against the Gram-positive viz. Bacillus subtilis, Staphylococcus aureus and Gramnegative viz. Pseudomonas aeruginosa bacteria. The compounds A2 and A5 containing thiosemicarbazide moiety showed good spectrum of activity with MIC values of 31.25μg/ml.