Synthesis, spectroscopy, crystal structure, TGA/DTA study, DFT and molecular docking investigations of (E)-4-(4-methylbenzyl)-6-styrylpyridazin-3(2H)-one

Fouad El Kalai; Emine Berrin Çınar; Chin-Hung Lai; Said Daoui; Tarik Chelfi; Mustapha Allali; Necmi Dege; Khalid Karrouchi; Noureddine Benchat

doi:10.1016/j.molstruc.2020.129435

Synthesis, spectroscopy, crystal structure, TGA/DTA study, DFT and molecular docking investigations of (E)-4-(4-methylbenzyl)-6-styrylpyridazin-3(2H)-one

J Mol Struct. 2021 Mar 15:1228:129435. doi: 10.1016/j.molstruc.2020.129435. Epub 2020 Oct 10.

Authors

Fouad El Kalai¹, Emine Berrin Çınar², Chin-Hung Lai^{3

4}, Said Daoui¹, Tarik Chelfi¹, Mustapha Allali⁵, Necmi Dege², Khalid Karrouchi⁶, Noureddine Benchat¹

Affiliations

¹ Laboratory of Applied Chemistry and Environment (LCAE), Department of Chemistry, Faculty of Sciences, Mohammed I University, Oujda 60000, Morocco.
² Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139, Samsun, Turkey.
³ Department of Medical Applied Chemistry, Chung Shan Medical University, Taichung 40241, Taiwan.
⁴ Department of Medical Education, Chung Shan Medical University Hospital, 402 Taichung, Taiwan.
⁵ Institute of Nursing Professions and Health Techniques Fez, EL Ghassani Hospital, Fez 30000, Morocco.
⁶ Laboratory of Analytical Chemistry and Bromatology, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco.

Abstract

In this study, we present the synthesis of novel pyridazin-3(2H)-one derivative namely (E)-4-(4-methylbenzyl)-6-styrylpyridazin-3(2H)-one (MBSP). The chemical structure of MBSP was characterized using spectroscopic techniques such as FT-IR, ¹H NMR, ¹³C NMR, UV-Vis, ESI-MS, and finally, the structure was confirmed by single X-ray diffraction studies. The DFT calculation was performed to compare the gas-phase geometry of the title compound to the solid-phase structure of the title compound. Furthermore, a comparative study between theoretical UV-Vis, IR, ¹H- and ¹³C NMR spectra of the studied compound and experimental ones have been carried out. The thermal behavior and stability of the compound were analyzed by using TGA and DTA techniques which revealed that the compound is thermostable up to its melting point. Finally, the in silico docking and ADME studies are performed to investigate whether MBSP is a potential therapeutic for COVID-19.

Keywords: Crystal structure, DFT, Hirshfeld surface; Molecular docking; Pyridazin-3(2h)-one; Synthesis; Thermal analysis.