Synthesis, Biological Activity, and Computational Study of 1-[5-(4-Methylthiazol-5-yl)-2-phenyl-1,3,4-oxadiazol-3(2H)-yl]ethanone Derivatives

• Published in: Russian journal of general chemistry 2022-08, Vol.92 (8), p.1511-1518
• Main Authors: Darekar, Nirmala R., Takate, Sushama J., Akolkar, Hemant N., Shaikh, Mubarak H., Khedkar, Vijay M., Karale, Bhausaheb K., Mhaske, Sadhana D.
• Format: Article
• Language: English
• Subjects: Bioavailability; Biological activity; Biological computing; Chemical compounds; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Fungicides; Mass spectra; Molecular docking; NMR; Nuclear magnetic resonance; Pharmacology; Synthesis
• ISSN: 1070-3632; 1608-3350
• DOI: 10.1134/S1070363222080199

A simple and efficient method of synthesis of 1-[5-(4-methylthiazol-5-yl)-2-phenyl-1,3,4-oxadiazol-3(2 H )-yl]ethanone from ( E )- N ′-benzylidene-4-methylthiazole-5-carbohydrazides and acetic anhydride has been developed. Structures of the synthesized compounds have been confirmed by IR, 1 H and 13 C NMR, and mass spectra. All compounds have been tested for their in vitro antibacterial and antifungal activity. Molecular docking study has been carried out for deeper insight in the antimicrobial action and prediction of the binding modes of these compounds. In silico ADMET predictions and pharmacokinetic studies confirm high oral bioavailability of the products. The results of in vitro and in silico studies suggest that thiazole and oxadiazole incorporated heterocycles can match the structural requirements for further development of novel therapeutic agents.