Investigation of Novel Thiazolin-2,4-diones: Synthesis, Biological Evaluation, and Docking Studies for Enhanced Insights

Abstract

Objective: A newer series of compounds, including 3-benzoyl-5-(substituted-benzylidin)-thiazolidin-2,4-dione (IVa–IVh) and 3-p-tolyl-5-(substituted-benzylidine)-thiazolidin-2,4-dione (Va–Vh), were synthesized through a nucleophilic reaction involving benzoyl chloride and p-chlorotoluene. These compounds were obtained in conjunction with various 5-(substituted-benzylidine)-thiazolidin-2,4-dione derivatives, which were prepared by condensing thiazolidin-2,4-dione with different substituted benzaldehydes. Comprehensive structural characterization was achieved through UV, FT-IR, ¹H NMR, and mass spectroscopy. Methods: Antimicrobial assessment was conducted against a panel of bacterial strains including E. coli, S. aeruginosa, S. aureus, and B. subtilis, as well as fungal strains A. niger and C. albicans. Molecular docking studies were employed to further validate the results. Anticancer activity was evaluated using the sulforhodamine B (SRB) assay on the HEPG2 cell line. Results and Discussion: The synthesized compounds demonstrated significant antibacterial activity against E. coli, S. aeruginosa, S. aureus, and B. subtilis. Furthermore, notable antifungal activity was observed against A. niger and C. albicans. Compound (Vd) displayed exceptional performance in both aspects, confirmed by molecular docking. Additionally, (IVc), (Vc), (IVh), and (Vh) exhibited significant anticancer activity, while (IVd) exhibited moderate activity at varying concentrations. Conclusions: The newly synthesized compounds exhibit promising antimicrobial and anticancer properties, indicating their potential for pharmaceutical applications. This research represents a significant advancement in medicinal chemistry, offering avenues for further drug development and exploration in the field.