Synthesis, Biological Evaluation, and in-Silico Molecular Docking Studies of Multifunctional Thiazolidine Derivatives

Abstract

Herein we report the synthesis and biological evaluation of a new series of thiazolidin-4-one derivatives. The C4 and C5 functionalized, 5-arylidene/alkylidene, 5-bromo, 5-pyridinium, and 4-arylimino analogs of thiazolidine-4-one were prepared efficiently using appropriate synthetic routes and characterized by IR, NMR and Mass spectrometry. Results of antimicrobial evaluation showed that compounds 4 and 8 had significant antibacterial activity comparable to that of the reference drug gentamicin. Compound 5a showed promising antifungal activity compared to amphotericin B as a reference drug. The antitumor activity revealed that compound 4 was the most active analog among the tested series with IC₅₀ values of 28.4 and 12.6 µg/mL against both HCT-116 and HepG-2 cell lines, respectively, compared to standard drug doxorubicin. Results from the biological evaluation, in-silico molecular docking studies, and ADMET analyses confirmed that thiazolidin-4-one is a promising scaffold that can be used to design potential lead compounds for the antibacterial and antitumor agents.

Keywords:

• Thiazolidin-4-one
• antibacterial
• antifungal
• cytotoxicity
• structure-activity relationship

Acknowledgment

The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding this work through the Large Groups Project under grant number (RGP2/381/44). The authors would also like to acknowledge the OpenEye Scientific software for providing the academic license.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was supported by King Khalid University [RGP2/381/44].