Structure elucidation, DFT and IRI computational investigations of a novel 4-(3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile

Abstract

A novel symmetric dihydropyridine possessing cyano group at C11 and C14 has been synthesized using a modified Hantzsch method. The compound (▪) was characterized spectroscopically by Mass, IR and 1H NMR methods and finally confirmed by X-ray diffraction study. The compound crystallizes in a monoclinic crystal class with P21/c space group. In the title molecule, the dihydropyridine ring is puckered and displayed an envelope conformation of the type E1. The solid state of the title compound is governed by an intermolecular C–H…N, C–H…Cl and C–H…π interactions in the building of a crystal. It is investigated by three dimensional Hirshfeld surfaces mapped on different properties, also the relevant fingerprint graphs are obtained to recognize the percentage contribution from various inter atomic contacts. The topology of three dimensional interaction energy frameworks were constructed using the energy density wave function of DFT/B3LYP/6-311++G(d,p) and the energy corresponding to intermolecular interactions were assessed. The density functional theory analysis has been carried out and hence an energy gap and global index parameters are evaluated, also the geometric parameters are computed by optimizing the molecular structure of the title compound. The natural bonding orbitals (NBO) analysis is carried out to know the intermolecular charge transfer in the molecule. Reduced density gradients (RDG) and interaction region indicators (IRI) analysis reveals the chemical bonding and weak interactions regions. The molecular docking has been performed on 1B38, 2OHM, 3VNT and 4URO receptors shows good binding affinities and their results reveal that it serves as potential anti-cancer agent.