Synthesis, crystal structure, Hirshfeld surface, computational and antibacterial studies of a 9-phenanthrenecarboxaldehyde-based thiodihydropyrimidine derivative

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dc.authoridHuseynzada, Alakbar/0000-0002-6342-4260
dc.authoridMENEGHETTI, FIORELLA/0000-0002-6511-7360
dc.authoridAbbasov, Vagif/0009-0003-9270-6624
dc.authoridChiarelli, Laurent Roberto/0000-0003-0348-9764
dc.authoridMori, Matteo/0000-0002-7491-1494
dc.contributor.authorHuseynzada, Alakbar
dc.contributor.authorMori, Matteo
dc.contributor.authorMeneghetti, Fiorella
dc.contributor.authorIsrayilova, Aygun
dc.contributor.authorTuzun, Gamze
dc.contributor.authorSayin, Koray
dc.contributor.authorChiarelli, Laurent R.
dc.date.accessioned2024-10-26T18:11:33Z
dc.date.available2024-10-26T18:11:33Z
dc.date.issued2022
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractWe report herein the synthesis of a new biologically active 3,4-dihydropyrimidin-2(1H)-thione derivative ( 4 ) from 9-phenanthrenecarboxaldehyde, thiourea, and methyl acetoacetate by the Biginelli reaction. The structure of the synthesized compound was investigated by NMR spectroscopy, mass spectrometry, and elemental analysis. Moreover, to gain insight into the conformation and crystal packing, the structure of the novel dihydropyrimidine was also studied by single-crystal X-ray diffraction. The Hirshfeld surface and contact enrichment analyses were used to better understand the molecular interactions. Considering the biological activity of dihydropyrimidines, the antibacterial effect of the synthesized compound was evaluated against A. baumanii, E. coli, P.aeruginosa, K. pneumoniae, and S. aureus; interestingly, high activ-ity was detected against S. aureus. Additionally, computational studies were performed using the Gaussian package and the Maestro Schrodinger programs, and the theoretical IR and NMR spectra of compound 4 were examined. Finally, an ADME/T analysis was performed to estimate the drug-likeness of the com-pound.(c) 2022 Elsevier B.V. All rights reserved.
dc.description.sponsorshipErasmus + overseas [ICM KA107]; Science Development Foundation; TUBITAK [EIF-BGM-5-AZTURK-1/2018-2/02/4-M-02]; Scientific Research Project Fund of Sivas Cumhuriyet University [RGD-020]
dc.description.sponsorshipThis work was supported by the Erasmus + overseas/ICM KA107 program, Science Development Foundation under the President of the Republic of Azerbaijan and TUBITAK in the frames of the project number EIF-BGM-5-AZTURK-1/2018-2/02/4-M-02 and by the Scientific Research Project Fund of Sivas Cumhuriyet University under the project number RGD-020. This research was made possible by TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e -Infrastructure) .
dc.identifier.doi10.1016/j.molstruc.2022.133571
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85133529251
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2022.133571
dc.identifier.urihttps://hdl.handle.net/20.500.12418/30732
dc.identifier.volume1267
dc.identifier.wosWOS:000828407000009
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/openAccess
dc.subjectThiodihydropyrimidine
dc.subjectHirshfeld surface analysis
dc.subjectCrystal structure
dc.subjectMolecular docking
dc.subjectADME
dc.subjectT
dc.titleSynthesis, crystal structure, Hirshfeld surface, computational and antibacterial studies of a 9-phenanthrenecarboxaldehyde-based thiodihydropyrimidine derivative
dc.typeArticle

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