Synthesis, characterization, computational studies and biological activities of novel NHC precursor and its silver (I) and selenium compounds

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dc.contributor.authorSerin, Sumeyya
dc.contributor.authorKarakas, Gulsen
dc.contributor.authorMumcu, Akin
dc.contributor.authorUlu, Oznur Dogan
dc.contributor.authorDik, Gamze
dc.contributor.authorUtku, Tugba
dc.contributor.authorAtes, Burhan
dc.date.accessioned2026-04-04T13:34:54Z
dc.date.available2026-04-04T13:34:54Z
dc.date.issued2025
dc.departmentİnönü Üniversitesi
dc.description.abstractThe potential applications of fluorine in drug design are expanding rapidly. The evolution of synthetic methodologies has engendered the conception of novel fluorinated motifs. In the present study, the effective use of N-heterocyclic carbenes (NHCs) in pharmaceutical chemistry was combined with the enhancing role of fluorine groups in bioactivity, and the synthesis of a new NHC precursor (1) containing 2,6-difluorobenzyl group was achieved. Respective Ag-NHC (2) and Se-NHC (3) compounds were prepared from the synthesized NHC precursor. Structural characterization of each compound (1-3) was conducted by H-1, C-13 and F-19 NMR, FT-IR, UV-visible spectroscopy, and elemental analysis methods. The antioxidant activity of these compounds was evaluated by using ABTS and DPPH radical scavenging assays as well as their ability to inhibit the acetylcholine esterase (AChE) enzyme. Besides, density functional theory (DFT) computations were performed in order to comparatively peruse the molecular structures, electronic properties, reactivity tendencies, donor-acceptor interactions, and electrostatic surface properties of compounds 1-3 for both vacuum and CHCl3 phase. The reactivity ranking for the gas phase was clearly determined to be 3 < 2 < 1, based on the calculated energy gap values. The excited state characteristics of 1-3 in CHCl3 were calculated by the TD-DFT method. The antioxidant activity showed that the compounds, particularly compound 3 displayed effective antioxidant activities. According to the enzyme inhibition outcomes, compound 2 (IC50 value 8.43 +/- 0.71 mu M) had the most effective AChE inhibition among the synthesized compounds. Taken together, this investigation revealed the synthesis, characterization of various novel compounds (1-3) with, antioxidant potentials, AChE inhibitory activities, and quantum chemical calculations.
dc.description.sponsorshipInonue University [FBG-2023-3144]
dc.description.sponsorshipThe authors are gratefully thankful to I center dot no nu University for providing financial support (Project number: FBG-2023-3144) . The numerical calculations reported in this paper were fully performed at TUBITAK ULAKBIM. High Performance and Grid Computing Center (TRUBA re-sources) . The authors would also like to thank Assoc. Prof. Dr. Ahmet Ulu for his generous contributions.
dc.identifier.doi10.1016/j.molstruc.2025.142372
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.orcid0000-0002-5561-227X
dc.identifier.orcid0000-0002-4637-1734
dc.identifier.scopus2-s2.0-105002645618
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2025.142372
dc.identifier.urihttps://hdl.handle.net/11616/109483
dc.identifier.volume1339
dc.identifier.wosWOS:001474100200001
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_20250329
dc.subjectAg-NHC
dc.subjectSe-NHC
dc.subjectF-19 NMR
dc.subjectDFT calculation
dc.subjectReactivity indices
dc.subjectAntioxidant
dc.subjectEnzyme inhibition
dc.titleSynthesis, characterization, computational studies and biological activities of novel NHC precursor and its silver (I) and selenium compounds
dc.typeArticle

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