Spectroscopic, DFT study, and molecular docking investigation of N-(3-methylcyclohexyl)-2-phenylcyclopropane-1-carbohydrazide as a potential antimicrobial drug

Abstract

Detailed theoretical molecular modeling, spectral (NMR, FT-IR, and UV–vis) analysis, electronic properties, and in silico biological study of N-(3-Methylcyclohexyl)-2-phenyl cyclopropane-1-carbohydrazide (PI2) has been studied in this present research using experimental and electronic structure theory calculations based on density functional theory (DFT). While the quantum calculations were done using DFT method at the B3LYP/6-31+G(d) level of theory, the characterization of PI2 was carried out with 1HNMR, UV-vs, and FT-IR spectroscopy. The major vibrations recorded for the studied compound were those of amide, CC, C–C, N–H, and C–H stretch. The UV–visible excited states calculation using Time Dependent Density Functional Theory (TD-DFT) showed the highest orbital contributions in S0 – S5 with π→π* assignment for all the studied phases. The visual study of weak interaction (NCI), nonlinear optics, and the natural bond orbital (NBO) results showed majorly a steric effect due to strong repulsive forces and van der Waals forces, a better NLO property in the studied compound as compared with urea (standard) and the intramolecular charge transfer in the studied compound showed the highest energy of stabilization of 66.79KCal/Mol for the donor – acceptor interaction of LP (1) N23 → π*C25 - O26 respectively. Molecular docking investigation of PI2 was achieved using six (6) target proteins from which two were gram negative; Escherichia coli (2NYU) and Pseudomonas aeruginosa (7CID), 2 g positive; Staphylococcus aureus (6P9J) and Streptococcus pyogenes (1MG1), one helminth; Ascaris lumbricoides (3FJU) and one fungus; Candida albican (6TZ6). The PI2 docked results were compared with the docked results obtained for the standard drugs (Ciprofloxacin, Albendazole, and Fluconazole). The studied structure showed the highest binding affinity of −8.5 kcal/Mol for 1MG1 as compared with −6.9 kcal/Mol for that of the standard drug. Finally, ADMET properties of PI2 were computed and the result showed a better drug property of the studied compound.