Design, synthesis, and quantum chemical calculations of triazole-based aroylhydrazone molecules: Dual assessment of antioxidant properties via in vitro and in silico approaches

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dc.authoriddilek, omer/0000-0003-1409-782X
dc.authoridYESIL, Tolga Acar/0000-0001-5983-8447
dc.authoridDede, Bulent/0000-0003-1416-7373
dc.contributor.authorDilek, Omer
dc.contributor.authorYesil, Tolga Acar
dc.contributor.authorTilki, Tahir
dc.contributor.authorDede, Bulent
dc.date.accessioned2025-03-23T19:39:17Z
dc.date.available2025-03-23T19:39:17Z
dc.date.issued2025
dc.departmentSinop Üniversitesi
dc.description.abstractIn this study, five novel Triazole-Based Aroylhydrazone compounds (6a-e) were synthesized in high yields (87-79 %), starting from deferasirox which has known iron chelator, and characterized with NMR, FTIR, Mass, and UV-vis spectroscopic methods. Quantum chemical calculations of all synthesized molecules were performed at the DFT/B3LYP/6-311G(d,p) level. It was observed that both theoretical and experimental spectral values were compatible. Optimized molecular geometries were acquired from DFT calculations and used in molecular docking studies. Tyrosinase (PDB ID: 3NM8) protein was utilized in molecular docking studies. 6d-3NM8 complex had the highest docking score with the -10.1 kcal/mol. Stabilization of the 6d-3NM8 complex during 100 ns was determined via molecular dynamics simulation. Intramolecular interactions of all molecules were also examined by NCI-RDG analysis. The frequently used cupric ion reducing antioxidant capacity method (CUPRAC) was used to determine the antioxidant activity of synthesized compounds and Trolox which is unknown in the literature on its activity in DMSO. The highest TEAC value was 1.76 (6d) while the lowest one was 1.34 (6e). It is possible to say that the synthesized molecule 6d has the potential to be an antioxidant reagent based on the results of in vitro and in silico antioxidant activity.
dc.description.sponsorshipHarran University Application and Research Center for Science and Technology
dc.description.sponsorshipThe authors thank Harran University Application and Research Center for Science and Technology (HUBTAM) for NMR measurements of compounds.
dc.identifier.doi10.1016/j.molstruc.2024.140502
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85208553050
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2024.140502
dc.identifier.urihttps://hdl.handle.net/11486/6310
dc.identifier.volume1322
dc.identifier.wosWOS:001356318800001
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_20250323
dc.subjectDeferasirox
dc.subjectAntioxidant activity
dc.subjectCUPRAC
dc.subjectMolecular docking
dc.subjectMolecular dynamics simulation
dc.titleDesign, synthesis, and quantum chemical calculations of triazole-based aroylhydrazone molecules: Dual assessment of antioxidant properties via in vitro and in silico approaches
dc.typeArticle

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