One-pot synthesis, Spectral, X-ray crystal structure, Hirshfeld surface and computational study on potential inhibitory action of novel 1-benzyl-2-(4-methoxynaphthalen-1-yl)-4,5-diphenyl-1H-imidazole derivatives against COVID-19 main protease (Mpro: 6WCF/6Y84)

Abstract

A novel compound of 1-benzyl-2-(4-methoxynaphthalen-1-yl)-4,5-diphenyl-1H-imidazole (BMNDPI) are conveniently synthesized and characterized by spectral analysis FT-IR, 1H NMR, 13C NMR, Mass spectral and density functional theory (DFT/B3LYP/6–31 G (d, p) computations. The compound BMNDPI was also confirmed by single crystal XRD. The calculated geometric parameters are consistent with XRD data. To explore the intermolecular interactions, the generated Hirshfeld surface has been investigated along with 2D-fingerprint plots. The NBO results reflect the charge transfer is mainly by the orbital overlap between n (LPN54/LPO56) and σ * C1-N55/C43-C48 bond orbital which results intra-molecular charge transfer (ICT) causing stabilization of the system. Stability and charge transfer within the compound was explained by frontier molecular orbital calculations. Atomic charges on the various atoms of BMNDPI obtained by Mulliken population analysis. Potential reactive sites of the BMNDPI compound have been identified by MEP which is mapped to the electron density surfaces. The reported molecule is used as a potential NLO material since it has a high μβ0 value. The molecular docking mechanism between BMNDPI ligand and COVID-19/6WCF and COVID-19/6Y84 receptors were studied to investigate the binding modes of these compounds at the active sites. Molecular docking outcomes have shown that the BMNDPI molecule can be considered as a potential agent against COVID-19/6WCF-6Y84 receptors.