Microwave assisted amberlite-IRA-402 (OH) ion exchange resin catalyzed synthesis of new benzoxazole scaffolds derived from antiinflammatory drugs aceclofenac and mefenamic acid as potential therapeutic agents for inflammation

• Published in: Journal of molecular structure Vol. 1200; p. 127092
• Main Authors: Angajala, Gangadhara, Subashini, Radhakrishnan, Aruna, Valmiki
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.01.2020
• Subjects: Amberlite-IRA-402 (OH); Anti-inflammatory; Antioxidant; Benzoxazole; COX-2; Amberlite-IRA-402 (OH); COX-2; Antioxidant; Anti-inflammatory; Benzoxazole
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2019.127092

An efficient microwave assisted synthesis of 2-substituted benzoxazole derivatives from antiinflammatory drugs aceclofenac and mefenamic acid using amberlite-IRA-402 (OH) ion exchange resin as a base catalyst were reported. The synthesized compounds were purified and characterized by 1H NMR, 13C NMR and Mass spectroscopy. In silico molecular docking studies were carried out to predict the binding affinity of the synthesized benzoxazole derivatives with COX-2 protein. Molecular Docking analysis showed that compounds 4 and 7 possess excellent binding affinity towards COX-2 with a docking score of −11.6 and −10.4 kcaL/mol respectively. The results obtained from in vitro antiinflammatory studies towards membrane stabilization and proteinase inhibitory activities showed that the synthesized benzoxazole compounds 4 and 7 possess better efficacy when compared to that of standards aceclofenac and etodolac with a percentage inhibition of 74.22 ± 0.15, 70.64 ± 0.24 for membrane stabilization and 75.19 ± 0.12, 71.80 ± 0.49 for proteinase enzyme assay at 100 μmoL/L. The synthesized compounds 4 and 7 were also evaluated for antioxidant activity which showed good inhibition (70.16 ± 0.31 and 68.25 ± 0.49) at 100 μmoL/L which was on Par to that of standard ascorbic acid. •Microwave assisted and amberlite-IRA-402 (OH) catalyzed synthesis of new benzoxazole scaffolds.•Shorter reaction time, simple work-up procedure, clean reaction profiles and excellent product yields.•Molecular modelling simulations of the synthesized derivatives as COX-2 antagonists.•In-vitro antiinflammatory evaluation through membrane stabilization and proteinase inhibitory assays.