1,3,4-thiadiazole Attached 2, 3- disubstituted Thiazolidinones Derivatives: Synthesis and Biological Evaluation

Abstract:

Background: Thiazolidinone derivatives are the subject of prominent importance since they have been seen as valuable intermediates for the formulating/synthesize of different heterocyclic derivatives and it gives various subsidiaries with every extraordinary kind of exercise. What’re more, researches show that derivatives having 1,3,4-Thiadiazole core/ nucleus have a wide scope of pharmacological potential that incorporates antifungal, antibacterial, antiviral, anticancer, antitubercular, anticonvulsant, antidiabetic and antioxidant. From the literature reviewed, both the nucleus was found to be active as antimicrobials, anti-inflammatory as well as anticancer agents. Materials and Methods: It has been planned to synthesize “1,3,4-thiadiazolyl-thiazolidin-4-one” derivatives and evaluate their biological activities. The novel subordinates (4a-4j) of 2, 3-disubstituted Thiazolidinones were integrated into acceptable yield by the synthesis of benzaldehyde with thiosemicarbazide to provide thiosemicarbazones, 1,3,4-thiadiazoles is then produced by thiosemicarbazone cyclized by involving ferric chloride. By the reaction of various aromatic aldehyde with 1,3,4-thiadiazoles yielded different Schiff bases. The final derivative 2-aryl-3-(5-aryl-1,3,4-thiadiazol-2-yl)- 1,3-thiazolidine-4-one was obtained by the reaction between the schiff base with thioglycolic acid. All subordinates/ derivatives were portrayed by spectral analysis examination (IR, 1H NMR) and elemental analysis and then screened for biological activities (in-vitro anticancer, antimicrobial, anti-inflammatory). Results and Conclusion: The analysis reveals that synthesized derivatives of thiazolidinone possessing methyl, hydro, nitro, hydroxyl, flouro, chloro, methoxy, dimethoxy and amino substitution through phenyl ring. All these groups help pharmacophore, to increase their pharmacological activities. However, the substituted phenyl ring in the side chain also facilitates the biological action of the molecules. The increased activity of the new derivatives explains that they act as a more powerful and potent bioactive molecule when compare with the standard drug. This significant activity may be due to the substitution in the 2nd position of thiazolidinone nucleus. As result, all the tested compounds exhibit good activity and compounds 4i, 4b, 4f and 4a were established more noteworthy and outstanding as of all the derivatives.

Key words: Schiff base, Thiazolidinone, 1,3,4-Thiadiazole, Molecular docking, Antiinflammatory, Antimicrobial, Anti-cancer.