Synthesis, Crystal Structure, and Computational Investigations of 2-(2-(4-Fluorophenyl)-2-oxoethyl)-6-methyl-5-(4-methylbenzyl)pyridazin-3(2H)-one as Antiviral Agent

被引:4
作者
El Kalai, Fouad [1 ]
Abraham, Christina Susan [2 ]
Kansiz, Sevgi [3 ]
Oulmidi, Afaf [4 ]
Muthu, Sambantham [5 ]
Prasana, Johanan Christian [2 ]
Dege, Necmi [6 ]
Abuelizz, Hatem A. A. [7 ]
Al-Salahi, Rashad [7 ]
Benchat, Noureddine [1 ]
Karrouchi, Khalid [8 ]
机构
[1] Mohammed I Univ, Fac Sci, Dept Chem, Lab Appl Chem & Environm LCAE, Oujda 60000, Morocco
[2] Madras Christian Coll, Dept Phys, East Tambaram 600059, India
[3] Samsun Univ, Fac Engn, Dept Fundamental Sci, TR-55420 Samsun, Turkiye
[4] Catholic Univ Louvain, Inst Condensed Matter & Nanosci Mol Chem Mat & Cat, B-1348 Louvain La Neuve, Belgium
[5] Arignar Anna Govt Arts Coll, Dept Phys, Cheyyar 604407, India
[6] Ondokuz Mayis Univ, Fac Arts & Sci, Dept Phys, TR-55139 Samsun, Turkiye
[7] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, POB 2457, Riyadh 11451, Saudi Arabia
[8] Mohammed V Univ Rabat, Fac Med & Pharm, Team Formulat & Qual Control Hlth Prod, Lab Analyt Chem & Bromatol, Rabat 10100, Morocco
关键词
pyridazinone; crystal structure; DFT; SARS-CoV-2; molecular docking; CHARGE-TRANSFER; BIOLOGICAL EVALUATION; HIRSHFELD SURFACE; MOLECULAR-DYNAMICS; DRUG DISCOVERY; PYRIDAZINONE; DFT; DERIVATIVES; HARDNESS; DOCKING;
D O I
10.3390/cryst13071098
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
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, H-1-NMR, C-13-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 (& omega;) 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.
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页数:18
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