A new series of benzoyl chloride-substituted 2,4-thiazolidinedione derivatives have been synthesized by the condensation of 2-amino-4-aryl-thiazole and 40 -chlorosulfonyl benzylidine-2,4-thiazolidinedione. New compounds were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa. Furthermore, new products were tested for in vitro antituberculosis activity against Mycobacterium tuberculosis using isoniazid and rifampicin as control drugs. The results of bioassay demonstrated that some of the newly synthesized 2,4 thiazolidinedione derivatives emerged as lead molecules with excellent MIC (mg/mL) values against mentioned organisms compared to standard drugs. The structure of the final analogs has been confirmed on the basis of IR, 1 H NMR, mass spectral, and elemental analysis.