Sonochemical synthesis of New Thiazolidin-4-one derivatives as potent anticancer and antimicrobial agents with Docking design, and Energy gap estimation

Abstract

Thiazolidin-4-ones have important biological features, which has led to the development of new derivatives employing an efficient ultrasonic method. Schiff base derivatives were synthesized by condensation of 4,4′-diaminophenylmethane with various substituted benzaldehyde. These derivatives are subsequently subjected to cyclization, leading to the formation of thiazolidine-4-ones with favorable yields. The synthesized compounds were characterized using various analytical techniques such as FT-IR, 1H and 13C NMR, HRMS spectroscopy, and CHNS analysis. Thiazolidin-4-ones demonstrated anticancer potential with percentage cell viability at different concentrations (1mM, 3mM, and 5mM) and cell toxicity (1mM, 3mM, and 5mM). The IC50 values of compound 4g were found to be (72.27±1.39, 67.28±1.63, and 63.22±1.82), (36.77±0.11, 32.71±0.31, and 32.71±0.31), and 10.77±0.95, respectively. It is a good result according to the standard. The tested compounds demonstrated remarkable antimicrobial efficacy against bacterial strains like Staphylococcus aureus, Escherichia coli, and the fungal strain Candida albicans. The Minimum Inhibitory Concentrations (MIC) of compound 4g against Staphylococcus aureus, Escherichia coli, and Candida albicans were found to be 0.50±0.027, 0.70±0.040, and 0.80±0.036, respectively, which are comparable to reference medications. Docking design was conducted with the Staphylococcus aureus MurB protein (ID Code: 1HSK) and Novel CDK-5 inhibitor EFP crystal structure with CDK-2 (ID Code: 3IG7) for colon carcinoma HT29. Finally, the energy gaps were estimated by calculating HUMO and LUMO energy levels using the DFT/B3LYP method with the 6-31 G (d, p) basis set.