Synthesis of new fluorinated sulfonates and their Schiff bases as anti-Alzheimer drug candidates: An in vitro-in silico study

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dc.contributor.authorÇakmak, Reşit
dc.contributor.authorBaşaran, Eyüp
dc.contributor.authorErcan, Selami
dc.contributor.authorBoğa, Mehmet
dc.contributor.authorÇınar, Ercan
dc.contributor.authorTopal, Giray
dc.date.accessioned2025-02-22T14:10:54Z
dc.date.available2025-02-22T14:10:54Z
dc.date.issued2025
dc.departmentDicle Üniversitesien_US
dc.description.abstractIn this research, we designed and synthesized a series of new 3- or 4-(trifluoromethyl)- substituted sulfonate esters (1–14) linked heterocyclic Schiff base derivatives (15–28) as potential inhibitors of acetylcholinesterase and butyrylcholinesterase. The chemical structures of the target compounds were elucidated using elemental analysis and various spectral techniques. In vitro inhibitory results revealed IC50 values ranging from 12.05±0.10 to 43.08±0.20 μM against acetylcholinesterase and 0.42±0.04 to 95.52±0.00 μM against butyrylcholinesterase. Among the tested compounds, most sulfonates were found to inhibit acetylcholinesterase better than butyrylcholinesterase. In contrast, their Schiff base derivatives inhibited butyrylcholinesterase more effectively acetylcholinesterase did. Compounds 19, 20, and 21 inhibited butyrylcholinesterase better than galanthamine. The effects of trifluoromethyl group at positions 3 or 4 of the sulfonate moiety and the biosubstitutions at position R2 of the spacer moiety on the inhibitory activities were evaluated. Moreover, the antioxidant potency of these compounds was assessed by three different assays (DPPH free radical scavenging activity, ABTS cationic radical decolorization, and cupric reducing antioxidant capacity. The newly synthesized derivatives showed very low antioxidant activity (>1000 μM) in the DPPH and ABTS assays, while some of 3- trifluoromethyl substituted Schiff base derivatives (compounds 15, 20, and 21) showed activity closer to α-tocopherol in cupric reducing antioxidant capacity assay. The binding modes and binding free energies for acetylcholinesterase and butyrylcholinesterase inhibitor candidates were determined through docking studies. Taken together, we consider some inhibitor candidates to be valuable lead structures that can be used in further studies to design new anti-Alzheimer's disease drugs. © 2025 Elsevier B.V.en_US
dc.identifier.doi10.1016/j.molstruc.2025.141474
dc.identifier.issn0022-2860
dc.identifier.scopus2-s2.0-85215359236en_US
dc.identifier.scopusqualityQ1en_US
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2025.141474
dc.identifier.urihttps://hdl.handle.net/11468/29868
dc.identifier.volume1329en_US
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherElsevier B.V.en_US
dc.relation.ispartofJournal of Molecular Structureen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.snmzKA_Scopus_20250222
dc.subjectAntioxidant activityen_US
dc.subjectAntipyrineen_US
dc.subjectCholinesterase inhibitoryen_US
dc.subjectMolecular dockingen_US
dc.subjectSchiff baseen_US
dc.titleSynthesis of new fluorinated sulfonates and their Schiff bases as anti-Alzheimer drug candidates: An in vitro-in silico studyen_US
dc.typeArticleen_US

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