Novel Schiff Bases: Synthesis, Characterization, Bioactivity, Cytotoxicity, and Computational Evaluations

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dc.contributor.authorMedetalibeyoğlu, Hilal
dc.contributor.authorManap, Sevda
dc.contributor.authorAlkan, Muzaffer
dc.contributor.authorBeytur, Murat
dc.contributor.authorBarlak, Neslisah
dc.contributor.authorKaratas, Omer Faruk
dc.contributor.authorTüzün, Burak
dc.date.accessioned2024-10-26T17:51:44Z
dc.date.available2024-10-26T17:51:44Z
dc.date.issued2024
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractHypopharyngeal cancer is rare subtype of head and neck cancers with relatively poor prognosis. Current therapeutic modalities lack the potential to provide patients with better clinical outcome and quality of life. This study was conducted on the synthesis of 2-methoxy-4-((3-alkyl(aryl)-5-oxo-1H-1,2,4-triazol-4(5H)-ylimino)-methyl)-phenyl-4-(2-methoxy-4-((3-alkyl(aryl)-5-oxo-1H-1,2,4-triazol-4(5H)-ylimino)-methyl)-phenyl)-4-oxobutanoates (3) using biologically important 1,2,4-triazole. The condensation of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1) with 4-formyl-2-methoxyphenyl-4-(4-formyl-2-methoxyphenyl)-4-oxobutanoate yielded the biologically active 2-methoxy-4-((3-alkyl(aryl)-5-oxo-1H-1,2,4-triazol-4(5H)-ylimino)-methyl)-phenyl-4-(2-methoxy-4-((3-alkyl(aryl)-5-oxo-1H-1,2,4-triazol-4(5H)-ylimino)-methyl)-phenyl)-4-oxobutanoates (3). The compounds obtained were analyzed via FT-IR,1H-/13C-NMR spectrometers, elemental analysis, and HRMS spectroscopic techniques. Furthermore, we aimed at investigating the potential of compounds 3a-g against FaDu hypopharyngeal cancer cells. We demonstrated that compounds 3c, 3e, and 3 g had relatively lower IC50 values compared to the remaining tested compounds and more importantly their IC50 values were comparable to 5-FU, which suggests them as important therapeutic agent candidates. These newly synthesized compounds were assessed for their inhibitory activities toward two human carbonic anhydrase isoforms I and II (hCA I and II). Then, molecular docking calculations were made to compare the biological activities of studied molecules against cancer proteins. Compound 3c has a docking score of ?7.15 against squamous cell carcinoma protein with ID: 2DO4 and ?5.49 docking score against squamous cell carcinoma protein with ID:5PJZ. ADME/T analysis was performed to examine the drug properties of studied molecules. © 2024 Taylor & Francis Group, LLC.
dc.identifier.doi10.1080/10406638.2024.2412217
dc.identifier.issn1040-6638
dc.identifier.scopus2-s2.0-85205668534
dc.identifier.scopusqualityQ3
dc.identifier.urihttps://doi.org/10.1080/10406638.2024.2412217
dc.identifier.urihttps://hdl.handle.net/20.500.12418/26393
dc.identifier.wosWOS:001330436500001
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherTaylor and Francis Ltd.
dc.relation.ispartofPolycyclic Aromatic Compounds
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectADME/T; azomethine; biological activity; cell culture; molecular docking; Schiff bases
dc.titleNovel Schiff Bases: Synthesis, Characterization, Bioactivity, Cytotoxicity, and Computational Evaluations
dc.typeArticle

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