Synthesis, anti‐inflammatory activity, and molecular docking study of novel azo bis antipyrine derivatives against cyclooxygenase‐2 enzyme. Issue 1 (17th November 2020)

• Record Type: Journal Article
• Authors: Bhuvaneswari, Kaliyan; Nagasundaram, Nagarajan; Lalitha, Appaswami
• Is Part Of: Journal of the Chinese Chemical Society. Volume 68:Issue 1(2021)
• Page Start: 27
• Page End: 33
• Publication Date: 2020-11-17
• Subjects: azo bis antipyrine -- anti‐inflammatory activity -- docking studies -- COX‐2; Chemistry -- Periodicals; Electronic journals; 540.5
• DOI: 10.1002/jccs.202000265
• Languages: English
• ISSNs: 0009-4536

Abstract

Abstract: We have synthesized a new series of azo‐bis antipyrine derivatives from a one‐pot multicomponent Knoevenagel/Michael addition reaction of antipyrine, with a diversity of azo aldehydes in ethanol and L‐Proline as a catalyst under reflux condition. The anti‐inflammatory activity of the final products was assessed using the inhibition of albumin denaturation technique. Compound 3f showed an inhibitory effect with IC50 values of 3.6 μM with respect to the standard anti‐inflammatory drug Aspirin, with IC50 values of 2 μM. In addition, molecular docking was performed to confirm the in vitro results against the enzymatic inhibition activity of COX‐2 enzymes in which compound 3f showed good binding affinity with an inhibition constant (Ki) of 1.79 nM. Abstract : Nine novel azo‐bis antipyrine derivatives were synthesized. Docking of compound 3f showed good binding affinity with the active site of cyclooxygenase‐2 enzyme (PDB: 6COX). Compound 3f showed an inhibitory effect with IC50 values of 3.6 μM with respect to the standard anti‐inflammatory drug Aspirin with IC50 values of 2 μM.