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

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  1 , Emine Berrin Çınar  2 , Chin-Hung Lai  3   4 , Said Daoui  1 , Tarik Chelfi  1 , Mustapha Allali  5 , Necmi Dege  2 , Khalid Karrouchi  6 , Noureddine Benchat  1
Affiliations

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 et al. J Mol Struct. .

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.

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Conflict of interest statement

All authors declare that there are no conflicts of interest.

Figures

Fig. 1
Fig. 1
Example of drugs with pyridazinone ring.
Fig. 2
Fig. 2
The molecular structure of MBSP, with atom labeling. Displacement ellipsoids are drawn at the 40% probability level (a), visualizing of dihedral angles within the molecule (b).
Fig. 3
Fig. 3
Packing diagrams with intermolecular interactions of the title compound.
Fig 4
Fig. 4
The B3LYP-optimized geometries of the title compound (bond lengths in Å; nitrogen in blue, oxygen in red, carbon in gray, hydrogen in white).
Fig. 5
Fig. 5
The molecular electrostatic potential for MBSP (the isodensity value= 0.0004).
Fig 6
Fig. 6
Experimental (a) and simulated (b) FT-IR spectra of the title compound.
Fig 7
Fig. 7
Experimental (a) and simulated (b) UV–vis spectra of the title compound.
Fig 8
Fig. 8
The frontier orbitals of MBSP (the isodensity value = 0.02).
Fig 9
Fig. 9
The experimental (a) 1H and (b) 13C NMR spectra of MBSP.
Fig 10
Fig. 10
dnorm mapped on Hirshfeld surfaces for visualizing the interactions of the title compound.
Fig 11
Fig. 11
Curvedness and shape indexes are shown for MBSP.
Fig 12
Fig. 12
Fingerprint plots of the whole molecules and the most effective interactions.
Fig 13
Fig. 13
TGA, DTA, and DrTGA curves of the title compound.
Fig 14
Fig. 14
The results of the docking studies of MBSP concerning the chosen targets.
Fig 14
Fig. 14
The results of the docking studies of MBSP concerning the chosen targets.
Fig 15
Fig. 15
The possible targets of MBSP.
Fig 16
Fig. 16
The SwissADME result.
Scheme 1
Scheme 1
Synthetic route of (MBSP).
See this image and copyright information in PMC

References

    1. Lee S.G., Kim J.J., Kim H.K., Kweon D.H., Kang Y.J., Cho S.D., Kim S.K., Yoon Y.J. Recent progress in pyridazin-3 (2H)-ones chemistry. Curr. Org. Chem. 2004;8:1463–1480.
    1. Giustiniano M., Mercalli V., Amato J., Novellino E., Tron G.C. Exploiting the electrophilic and nucleophilic dual role of nitrile imines: one-Pot, Three-component synthesis of furo [2, 3-d] pyridazin-4 (5 H)-ones. Org. Lett. 2015;17:3964–3967. - PubMed
    1. Suchand B., Satyanarayana G. Palladium-Catalyzed Acylation Reactions: a One-Pot Diversified Synthesis of Phthalazines, Phthalazinones and Benzoxazinones. Eur. J. Org. Chem. 2018;19:2233–2246.
    1. El-Ghaffar N.A., Mohamed M.K., Kadah M.S., Radwan A.M., Said G.H., Abd S.N. Synthesis and anti-tumor activities of some new pyridazinones containing the 2-phenyl-1H-indolyl moiety. J. Chem. Pharm. Res. 2011;3:248–259.
    1. Siddiqui A.A., Mishra R., Shaharyar M., Husain A., Rashid M., Pal P. Triazole incorporated pyridazinones as a new class of antihypertensive agents: design, synthesis and in vivo screening. Bioorg. Med. Chem. Lett. 2011;21:1023–1026. - PubMed

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