Synthesis, Antiinflammatory and Anti-microbial Evaluation Of Thiazolidinedione Derivatives

Abstract

A series of Schiff bases, 4(a-j) were synthesized from N-carbamoyl-4-[(1E,3E)-3-(2,4- dioxo-1,3-thiazolidin-5-ylidene)prop-1-en-1-yl]]benzenesulfonamide by condensation with different substituted aromatic aldehydes. The N-carbamoyl-4-[(1E,3E)-3-(2,4-dioxo- 1,3-thiazolidin-5-ylidene)prop-1-en-1-yl]]benzenesulfonamide was prepared from a chalcone, 5E-5-[(2E)-3-phenylprop-2-en-1-ylidene]-1,3-thiazolidine-2,4-dione via sulfonylation followed by amidation. The chalcone was obtained by Claisen Schmidt condensation of cinnamaldehyde with 1,3-thiazolidin-2,4-dione. The structures of new synthesized compounds were confirmed by IR, 1H NMR and Mass spectral data. Synthesized derivatives were evaluated for their anti inflammatory, antibacterial and antifungal activities. The synthesized compounds 4(a), 4(c) and 4(j) were found to possess significant anti inflammatory, antibacterial and antifungal activities. The docking studies were carried out in 2OYE, 1CX2, 1CQE, 1CVU and 1DCX receptors. The compound possessing nitro and methoxy group as substituent in phenyl ring exhibited good pharmacological activities than other synthesized derivatives.