Synthesis, Spectroscopy, Crystal Structure, TGA/DTA Study, DFT and Molecular Docking Investigations of ()-4-(4-methylbenzyl)-6-styrylpyridazin-3()-one

Overview

Journal J Mol Struct

Publisher Elsevier

Specialty Chemistry

Date 2020 Oct 19

PMID 33071353

Citations 8

Authors

Fouad El Kalai

Emine Berrin Cinar

Chin-Hung Lai

Said Daoui

Tarik Chelfi

Mustapha Allali

Necmi Dege

Khalid Karrouchi

Noureddine Benchat

Affiliations

Soon will be listed here.

Abstract

In this study, we present the synthesis of novel pyridazin-3()-one derivative namely ()-4-(4-methylbenzyl)-6-styrylpyridazin-3()-one (). The chemical structure of was characterized using spectroscopic techniques such as FT-IR, H NMR, C 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, H- and C 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 is a potential therapeutic for COVID-19.

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References

Daoui S, Baydere C, El Kalai F, Mahi L, Dege N, Karrouchi K . Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[5-(4-methyl-benz-yl)-6-oxo-3-phenyl-1,6-di-hydro-pyridazin-1-yl]acetic acid. Acta Crystallogr E Crystallogr Commun. 2019; 75(Pt 12):1925-1929. PMC: 6895937. DOI: 10.1107/S2056989019015317. View

Jacomini A, Silva M, Silva R, Goncalves D, Volpato H, Basso E . Synthesis and evaluation against Leishmania amazonensis of novel pyrazolo[3,4-d]pyridazinone-N-acylhydrazone-(bi)thiophene hybrids. Eur J Med Chem. 2016; 124:340-349. DOI: 10.1016/j.ejmech.2016.08.048. View

Daoui S, Cinar E, El Kalai F, Saddik R, Karrouchi K, Benchat N . Crystal structure and Hirshfeld surface analysis of 4-(4-methyl-benz-yl)-6-phenyl-pyridazin-3(2)-one. Acta Crystallogr E Crystallogr Commun. 2019; 75(Pt 9):1352-1356. PMC: 6727051. DOI: 10.1107/S2056989019011551. View

Lee , Yang , PARR . Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B Condens Matter. 1988; 37(2):785-789. DOI: 10.1103/physrevb.37.785. View

Sheldrick G . Crystal structure refinement with SHELXL. Acta Crystallogr C Struct Chem. 2015; 71(Pt 1):3-8. PMC: 4294323. DOI: 10.1107/S2053229614024218. View

Partap S, Akhtar M, Yar M, Hassan M, Siddiqui A . Pyridazinone hybrids: Design, synthesis and evaluation as potential anticonvulsant agents. Bioorg Chem. 2018; 77:74-83. DOI: 10.1016/j.bioorg.2018.01.001. View

OBoyle N, Banck M, James C, Morley C, Vandermeersch T, Hutchison G . Open Babel: An open chemical toolbox. J Cheminform. 2011; 3:33. PMC: 3198950. DOI: 10.1186/1758-2946-3-33. View

Weigend F, Ahlrichs R . Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy. Phys Chem Chem Phys. 2005; 7(18):3297-305. DOI: 10.1039/b508541a. View

Grosdidier A, Zoete V, Michielin O . Fast docking using the CHARMM force field with EADock DSS. J Comput Chem. 2011; 32(10):2149-59. DOI: 10.1002/jcc.21797. View

10.

Giustiniano M, Mercalli V, Amato J, Novellino E, Tron G . Exploiting the Electrophilic and Nucleophilic Dual Role of Nitrile Imines: One-Pot, Three-Component Synthesis of Furo[2,3-d]pyridazin-4(5H)-ones. Org Lett. 2015; 17(16):3964-7. DOI: 10.1021/acs.orglett.5b01798. View

11.

Kim Y, Jedrzejczak R, Maltseva N, Wilamowski M, Endres M, Godzik A . Crystal structure of Nsp15 endoribonuclease NendoU from SARS-CoV-2. Protein Sci. 2020; 29(7):1596-1605. PMC: 7264519. DOI: 10.1002/pro.3873. View

12.

Karrouchi K, Yousfi E, Sebbar N, Ramli Y, Taoufik J, Ouzidan Y . New Pyrazole-Hydrazone Derivatives: X-ray Analysis, Molecular Structure Investigation via Density Functional Theory (DFT) and Their High In-Situ Catecholase Activity. Int J Mol Sci. 2017; 18(11). PMC: 5713199. DOI: 10.3390/ijms18112215. View

13.

Pettersen E, Goddard T, Huang C, Couch G, Greenblatt D, Meng E . UCSF Chimera--a visualization system for exploratory research and analysis. J Comput Chem. 2004; 25(13):1605-12. DOI: 10.1002/jcc.20084. View

14.

El Kalai F, Baydere C, Daoui S, Saddik R, Dege N, Karrouchi K . Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chloro-benz-yl)-6-oxo-3-phenyl-1,6-di-hydro-pyridazin-1-yl]acetate. Acta Crystallogr E Crystallogr Commun. 2019; 75(Pt 6):892-895. PMC: 6658951. DOI: 10.1107/S2056989019007424. View

15.

Daoui S, Baydere C, El Kalai F, Saddik R, Dege N, Karrouchi K . Crystal structure and Hirshfeld surface analysis of ()-6-(4-hy-droxy-3-meth-oxy-styr-yl)-4,5-di-hydro-pyridazin-3(2)-one. Acta Crystallogr E Crystallogr Commun. 2019; 75(Pt 11):1734-1737. PMC: 6829713. DOI: 10.1107/S2056989019014130. View

16.

Abouzid K, Abdel Hakeem M, Khalil O, Maklad Y . Pyridazinone derivatives: design, synthesis, and in vitro vasorelaxant activity. Bioorg Med Chem. 2007; 16(1):382-9. DOI: 10.1016/j.bmc.2007.09.031. View

17.

Robertson D, Jones N, Krushinski J, Pollock G, Swartzendruber J, Hayes J . Molecular structure of the dihydropyridazinone cardiotonic 1,3-dihydro-3,3-dimethyl-5-(1,4,5,6-tetrahydro-6-oxo-pyridazinyl)- 2H-indol-2-one, a potent inhibitor of cyclic AMP phosphodiesterase. J Med Chem. 1987; 30(4):623-7. DOI: 10.1021/jm00387a007. View

18.

Kneller D, Phillips G, ONeill H, Tan K, Joachimiak A, Coates L . Room-temperature X-ray crystallography reveals the oxidation and reactivity of cysteine residues in SARS-CoV-2 3CL M: insights into enzyme mechanism and drug design. IUCrJ. 2020; 7(Pt 6). PMC: 7553146. DOI: 10.1107/S2052252520012634. View

19.

Livermore D, Bethell R, Cammack N, Hancock A, Hann M, Green D . Synthesis and anti-HIV-1 activity of a series of imidazo[1,5-b]pyridazines. J Med Chem. 1993; 36(24):3784-94. DOI: 10.1021/jm00076a005. View

20.

Grosdidier A, Zoete V, Michielin O . SwissDock, a protein-small molecule docking web service based on EADock DSS. Nucleic Acids Res. 2011; 39(Web Server issue):W270-7. PMC: 3125772. DOI: 10.1093/nar/gkr366. View