Molecular spectroscopic investigation, quantum chemical, molecular docking and biological evaluation of 2-(4-Chlorophenyl)-1-[3-(4-chlorophenyl)-5-[4-(propan-2-yl) phenyl-3, 5-dihydro-1H-pyrazole-yl] ethanone

Abstract

2-(4-Chlorophenyl)-1-[3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl-3, 5-dihydro-1H-pyrazole-yl] ethanone (CCPPE) has been studied experimentally and theoretically. The structure of CCPPE was characterized by X-ray diffraction (XRD), and determined theoretically by the ab initio Hartree-Fock (HF) method and by the density functional theory(DFT) method B3LYP using the 6-311++G (d, p) basis set. Theoretical topological analysis of the electron density, according to the Quantum Theory of Atoms in Molecule (AIM), electron localization function (ELF) and the localized orbital locator (LOL) have been performed. Fourier Transform Infrared (FTIR) and Fourier Transform Raman (FT-Raman) vibrational spectra were recorded and the observed frequencies were compared to those obtained from B3LYP/6-311G (d, p) and B3LYP/6-311++G (d, p) calculations. The HOMO and LUMO energy results show that good exchange of charge happened inside the molecule. Molecular electrostatic potential was also performed. From the MEP it is evident that the negative charges cover the C=O group, the region having the positive potential are over the phenyl rings and the remaining species are surrounded by zero potential. Theoretical (TD-DFT) and experimental UV-Vis absorption wavelengths (λ) were compared with each other. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. The antimicrobial activity of the CCPPE was determined against bacterial strains such as Bacillus subtilis,Staphylococcus aureus, E.coli, Pseudomonas and fungal strains such as Candida albicans and A.niger. The obtained results show that the compound exhibited good to moderate antimicrobial activity. Molecular docking studies were executed to understand the inhibitory activity of CCPPE against antibacterial, antifungal, anti-inflammatory, antioxidant, antiviral activities.