Synthesis, Crystal Structure, and Computational Investigations of 2-(2-(4-Fluorophenyl)-2-oxoethyl)-6-methyl-5-(4-methylbenzyl)pyridazin-3(2<i>H</i>)-one as Antiviral Agent
Fouad El Kalai,
Christina Susan Abraham,
Sevgi Kansiz,
Afaf Oulmidi,
Sambantham Muthu,
Johanan Christian Prasana,
Necmi Dege,
Hatem A. Abuelizz,
Rashad Al-Salahi,
Noureddine Benchat,
Khalid Karrouchi
Affiliations
Fouad El Kalai
Laboratory of Applied Chemistry and Environment (LCAE), Department of Chemistry, Faculty of Sciences, Mohammed I University, Oujda 60000, Morocco
Christina Susan Abraham
Department of Physics, Madras Christian College, East Tambaram 600059, India
Sevgi Kansiz
Department of Fundamental Sciences, Faculty of Engineering, Samsun University, Samsun 55420, Turkey
Afaf Oulmidi
Institute of Condensed Matter and Nanosciences, Molecular Chemistry, Materials and Catalysis (IMCN/MOST), Université Catholique de Louvain, 1348 Louvain-la-Neuve, Belgium
Sambantham Muthu
Department of Physics, Arignar Anna Government Arts College, Cheyyar 604407, India
Johanan Christian Prasana
Department of Physics, Madras Christian College, East Tambaram 600059, India
Necmi Dege
Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Samsun 55139, Turkey
Hatem A. Abuelizz
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
Rashad Al-Salahi
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
Noureddine Benchat
Laboratory of Applied Chemistry and Environment (LCAE), Department of Chemistry, Faculty of Sciences, Mohammed I University, Oujda 60000, Morocco
Khalid Karrouchi
Laboratory of Analytical Chemistry and Bromatology, Team of Formulation and Quality Control of Health Products, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, Rabat 10100, Morocco
The aim of this work was to scrutinize the physiochemical properties of a new pyridazin-3(2H)-one derivative with potential pharmaceutical effectiveness via density functional theory (DFT) and molecular docking analysis. The compound 2-(2-(4-fluorophenyl)-2-oxoethyl)-6-methyl-5-(4-methylbenzyl)pyridazin-3(2H)-one (FOMMP) was synthesized and characterized by FT-IR, UV-Vis, 1H-NMR, 13C-NMR, ESI-MS, and single-crystal XRD analysis. In addition, the geometrical structure of the molecule was analyzed. Frontier molecular orbital (FMO) analysis showed a low energy gap that suggests the chemical reactivity of the title compound. The electrophilicity index (ω) points towards the probable biological activity of FOMMP. The molecular electrostatic potential (MEP) was used to assess the local reactivity properties and suggests that the nitrogen atom sites are electronegative. Computational and experimental UV-spectral analyses were performed to attain the bandgap associated with electronic transitions while the charge transfer length helped us determine that the excitation mode associated with the electronic transitions is long-ranged. Natural hybrid orbital (NHO) and natural bond orbital (NBO) analyses depicted the prominent acceptor-donor interactions in terms of the stabilization energies. Hirshfeld surface analysis was performed to analyze the intermolecular interactions in the crystal structure. In addition, a molecular docking study was executed to evaluate the potential of the protease inhibitors (PIs) against SARS-CoV-2.
