Chalcone-based schiff bases: Design, synthesis, structural characterization and biological effects

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dc.authoridAydin Kose, Fadime/0000-0001-5222-7555
dc.authoridTUZUN, BURAK/0000-0002-0420-2043
dc.contributor.authorYalazan, Halise
dc.contributor.authorKoc, Damla
dc.contributor.authorKose, Fadime Aydin
dc.contributor.authorAkgul, Muhammed Ismail
dc.contributor.authorFandakli, Seda
dc.contributor.authorTuzun, Burak
dc.contributor.authorTaslimi, Parham
dc.date.accessioned2025-05-04T16:47:07Z
dc.date.available2025-05-04T16:47:07Z
dc.date.issued2025
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractThe presented work describes the synthesis, characterization, and biological effects of three new Schiff base compounds (SOH-F/Cl/Br) and their phthalonitrile derivatives (SCN-F/Cl/Br). The structures of all synthesized compounds were elucidated by NMR, FT-IR, and mass spectroscopic methods. Enzyme results were obtained at the nanomolar level. Cytotoxic activity of novel compounds was evaluated against neuroblastoma (SH-SY5Y) and mouse fibroblast (NIH-3T3) cell lines using MTT. It has been determined that all tested molecules have a powerful cytotoxic effect; IC50 values were under 10 mu M against SH-SY5Y cells. Among all compounds, the lowest IC50 value was observed in SCN-Br (1.798 +/- 0.036 mu M). Moreover, the IC50 concentration of SCN-Br (12.79 +/- 0.33 mu M) in healthy NIH-3T3 cells was significantly higher than in cancerous cells. The activity comparison of the studied six molecules was made with both DFT calculations and molecular docking calculations. Various proteins that are hCA I protein (PDB ID: 2CAB), hCA II protein (PDB ID: 5AML), and SH-SY5Y protein (PDB ID: 7LQZ, 5WIV, and 2F37) were used in molecular docking calculations. After this comparison, ADME/T calculations were used to analyze the molecules to be used as drugs.
dc.description.sponsorshipScientific Research Project Fund of Sivas Cumhuriyet University (CUBAP) [RGD-020]
dc.description.sponsorshipThe numerical calculations reported in this paper were fully/partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources). This work was supported by the Scientific Research Project Fund of Sivas Cumhuriyet University (CUBAP) under the project number RGD-020.
dc.identifier.doi10.1016/j.molstruc.2025.142211
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-105001868972
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2025.142211
dc.identifier.urihttps://hdl.handle.net/20.500.12418/35477
dc.identifier.volume1337
dc.identifier.wosWOS:001465272600001
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.snmzKA_WOS_20250504
dc.subjectChalcone
dc.subjectSchiff base
dc.subjectPhthalonitrile
dc.subjectEnzyme inhibition
dc.subjectMolecular docking
dc.subjectGaussian calculation
dc.titleChalcone-based schiff bases: Design, synthesis, structural characterization and biological effects
dc.typeArticle

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