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. 2021 Aug 14;59(4):511–521. doi: 10.1002/vjch.202000221

Synthesis of new 3‐(hydroxymethyl)‐2‐phenyl‐2,3 dihydroquinolinone and in‐silico evaluation of COVID‐19 main protease inhibitor

Amaladoss Nepolraj 1,✉, Vasyl I Shupeniuk 2, Manisekar Sathiyaseelan 1, Nagamuthu Prakash 3
PMCID: PMC8441664

Abstract

An exclusive approach towards the synthesis of novel 3‐(hydroxymethyl)‐2‐phenyl‐2,3 dihydroquinolin‐4(1H)‐one and it's in‐silico evaluation as inhibitor of COVID‐19 main protease. The one‐pot synthesis of an established procedure Claisen ester condensation reaction was sodium hydride mediated with intramolecular cyclization with solvent free conditions. The structures of the synthesized compound were confirmed by IR, 1H,13C NMR, and EI‐MS spectral studies. Chemo‐informatics study showed that the compound obeyed the Lipinski's rule, PASS, Swiss ADME. Computational docking analysis was performed using PyRx, AutoDock Vina option based on scoring functions. In‐silico molecular docking study results demonstrated Greater binding energy and affinity to the active pocket the N3 binding site of the Coronavirus primary protease.

Keywords: Methylantharanate, 2‐Phenylquinoline, Claisen condensation, molecular docking, RNA polymerase, protease Covid‐19

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