Crystal structure, Hirshfeld surface and DFT computations, along with molecular docking investigations of a new pyrazole as a tyrosine kinase inhibitor

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dc.authoridSaadi, Mohamed/0000-0003-2655-0230
dc.authoridChalkha, Mohammed/0000-0002-9400-2183
dc.authoridTUZUN, BURAK/0000-0002-0420-2043
dc.authoridBAKHOUCH, Mohamed/0000-0003-0732-6524
dc.authoridNAKKABI, Asmae/0000-0002-9845-243X
dc.contributor.authorChalkha, Mohammed
dc.contributor.authorel Hassani, Anouar Ameziane
dc.contributor.authorNakkabi, Asmae
dc.contributor.authorTuzun, Burak
dc.contributor.authorBakhouch, Mohamed
dc.contributor.authorBenjelloun, Adil Touimi
dc.contributor.authorSfaira, Mouhcine
dc.date.accessioned2024-10-26T18:09:52Z
dc.date.available2024-10-26T18:09:52Z
dc.date.issued2023
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractIn the present work we report the experimental and computational investigations of (2-aminophenyl)[4(4-chlorophenyl)-1,3-diphenyl-1H-pyrazol-5-yl]methanone (C 28 H 20 ClN 3 O). X-ray diffraction (XRD) showed that the undertaken compound 3 crystallized in a monoclinic system, space group P 2 1 / n . The structure exhibited both inter- and intramolecular hydrogen bonding contacts of the type N-H center dot center dot center dot X (X = O, N, Cl) and C-H center dot center dot center dot O, which ensured the stabilization of the crystal then the molecular structure. Hirshfeld surface analysis (HSA) showed that other unconventional interactions such as H center dot center dot center dot H (48%) and C center dot center dot H (28%) contributed as well in the molecular assembly. The energy of the HOMO and LUMO orbitals, the molecular electrostatic potential (MEP) and the absorption spectrum were generated using the density functional theory (DFT). The MEP map showed areas of the negative potential region around the electronegative atoms O1 and N3, while the maximum positive sites were around the hydrogen atoms of the amine group. The experimental and computed UV-Vis spectra showed the presence of pi- pi* and n- pi* transitions. The computational results showed that the geometrical and electronic parameters were consistent and in accordance with the experimental data. The anticancer activity of the studied pyrazole was investigated in-silico via molecular docking (MD) towards EGFR tyrosine kinases (PDB ID: 1M17 and 2ITN). The outcomes suggest that the pyrazole 3 has significant interaction with the target receptors. Afterwards, drug properties were investigated by ADME/T analysis, which show that the examined pyrazole 3 has an excellent pharmacokinetic profile and no toxicity risks.
dc.identifier.doi10.1016/j.molstruc.2022.134255
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85140755767
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2022.134255
dc.identifier.urihttps://hdl.handle.net/20.500.12418/30311
dc.identifier.volume1273
dc.identifier.wosWOS:000869407100001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectPyrazole
dc.subjectCrystal structure
dc.subjectElectronic properties
dc.subjectDFT
dc.subjectHirshfeld surface analysis
dc.subjectMolecular electrostatic potential
dc.subjectmolecular docking
dc.subjectADME
dc.subjectT analysis
dc.titleCrystal structure, Hirshfeld surface and DFT computations, along with molecular docking investigations of a new pyrazole as a tyrosine kinase inhibitor
dc.typeArticle

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