Synthesis, Cytotoxicity Assessment and Antioxidant Activity of Some New 4-Thiazolidinone Derivatives Containing 2-Methyl Furane Ring

Creative Commons License

Apaydin C. B., Ulbegi G. A. L. T. I. P. A. R. M. A. K., Sagirli P. A. K. S. O. Y., Goktas F. U. R.

JOURNAL OF RESEARCH IN PHARMACY, cilt.30, sa.5, ss.1232-1240, 2026 (ESCI, TRDizin)

Özet

4-Thiazolidinone derivatives bearing a 2-methyl furan ring are an important class of heterocyclic compounds with wide structural variability. These heterocyclic compounds are of increasing interest in medicinal chemistry due to their reported wide spectrum of pharmacological activities, including antioxidant and anticancer effects. In this study, a series of new 4-thiazolidinone derivative compounds bearing a furan ring system were synthesized, and their antioxidant and cytotoxic activities were investigated. Thiazolidinone compounds (2a-e, 3a-j) were synthesized by refluxing hydrazines and appropriate aldehydes or ketones with mercaptoacetic acid or 2-sulfanylpropanoic acid in toluene using Dean-Stark apparatus for 4 hours. The new compounds (2a-e) were characterized by IR, 1H NMR and 13C NMR (APT) spectral studies. The cytotoxic activities of all the compounds (2a-e, 3a-j) against lung (A549), prostate (PC-3) and endometrial (ECC-1) cancer cells, and non-cancerous Human Umbilical Vein Endothelial Cells (HUVEC), were tested in vitro using 3-[4,5-dimethylthiazol-2-yl]-5-[3-carboxymethoxyphenyl]- 2-[4-sulfophenyl]-2H-tetrazolium inner salt (MTS) assay. The antioxidant potentials of the compounds were evaluated by the Ferric Reducing Antioxidant Power (FRAP) and the 2,2-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity assays. The findings revealed that 3g demonstrated the highest DPPH. scavenging activity and ferric reducing antioxidant power. Furthermore, 3h exhibited the highest cytotoxic activity, however, 3d demonstrated selective cytotoxicity toward ECC-1 cells. In conclusion, the compounds displayed weak antioxidant properties but comparatively stronger cytotoxic effects. The selectivity of 3d suggests potential for further investigations.