2,4-Substituted Oxazolones: Antioxidant Potential Exploration

Abstract

Background: This study focuses on the development of a novel and environmentally friendly synthetic methodology for the production of a series of six 4-benzylidene-2-phenyloxazol- 5(4H)-one derivative (M1-M6). The approach involves a one-pot procedure utilizing hippuric acid, fused sodium acetate and various substituted aromatic aldehydes in the presence of acetic anhydride. Purpose: The primary objective is to explore the potential antioxidant properties of the synthesized compounds and contribute to the understanding of azlactones as promising antioxidants. The study integrates experimental synthesis with in silico methodologies to comprehensively characterize the chemical and biological properties of the derivatives. Materials and Methods: The synthesis process employed a combination of hippuric acid, fused sodium acetate and substituted aromatic aldehydes in a one-pot procedure. The chemical structures of the derivatives were characterized and validated through in silico techniques, including docking studies, drug-likeness assessments, bioactivity predictions, ADME profiling and toxicity evaluations. Results: The in silico analyses provided insights into the molecular interactions, pharmacokinetic properties and safety profiles of the synthesized compounds. In vitro antioxidant potential was systematically investigated using the DPPH method, with compounds M3 and M5 demonstrating significant antioxidant activity at a concentration 40 µg/ mL showing (88% inhibition) and (85.7% inhibition) respectively, surpassing ascorbic acid as the reference standard. Conclusion: This study successfully explores azlactones as potential antioxidants, combining experimental synthesis and in silico methodologies to characterize the chemical and biological properties of the synthesized derivatives. The notable antioxidant activity of compounds M3 and M5 positions them as promising candidates for further investigation. The findings establish a foundation for future research and development of these compounds in potential antioxidant-related therapeutic interventions.