Acetylphenyl-substituted imidazolium salts: synthesis, characterization, in silico studies and inhibitory properties against some metabolic enzymes

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dc.authoridDemir, Yeliz/0000-0003-3216-1098
dc.authoridTASKIN TOK, Tugba/0000-0002-0064-8400
dc.authoridAktaş, Aydın/0000-0001-8496-6782
dc.authoridGulcin, ilhami/0000-0001-5993-1668
dc.authoridTezcan, Burcu/0000-0001-5630-5522
dc.authorwosidDemir, Yeliz/ABI-5719-2020
dc.authorwosidTASKIN TOK, Tugba/A-8885-2016
dc.authorwosidAktaş, Aydın/J-6194-2019
dc.authorwosidGulcin, ilhami/F-1428-2014
dc.authorwosidGüzel, Bilgehan/D-1464-2018
dc.authorwosidTezcan, Burcu/GSN-1194-2022
dc.contributor.authorDemirci, Ozlem
dc.contributor.authorTezcan, Burcu
dc.contributor.authorDemir, Yeliz
dc.contributor.authorTaskin-Tok, Tugba
dc.contributor.authorGok, Yetkin
dc.contributor.authorAktas, Aydin
dc.contributor.authorGuzel, Bilgehan
dc.date.accessioned2024-08-04T20:53:14Z
dc.date.available2024-08-04T20:53:14Z
dc.date.issued2023
dc.departmentİnönü Üniversitesien_US
dc.description.abstractHerein, we present how to synthesize thirteen new 1-(4-acetylphenyl)-3-alkylimidazolium salts by reacting 4-(1-H-imidazol-1-yl)acetophenone with a variety of benzyl halides that contain either electron-donating or electron-withdrawing groups. The structures of the new imidazolium salts were conformed using different spectroscopic methods (H-1 NMR, C-13 NMR, F-19 NMR, and FTIR) and elemental analysis techniques. Furthermore, these compounds' the carbonic anhydrase (hCAs) and acetylcholinesterase (AChE) enzyme inhibition activities were investigated. They showed a highly potent inhibition effect toward AChE and hCAs with K-i values in the range of 8.30 & PLUSMN; 1.71 to 120.77 & PLUSMN; 8.61 nM for AChE, 16.97 & PLUSMN; 2.04 to 84.45 & PLUSMN; 13.78 nM for hCA I, and 14.09 & PLUSMN; 2.99 to 69.33 & PLUSMN; 17.35 nM for hCA II, respectively. Most of the synthesized imidazolium salts appeared to be more potent than the standard inhibitor of tacrine (TAC) against AChE and Acetazolamide (AZA) against CA. In the meantime, to prospect for potential synthesized imidazolium salt inhibitor(s) against AChE and hCAs, molecular docking and an ADMET-based approach were exerted.en_US
dc.description.sponsorshipInonu University Research Fund [FBG-2021-2525, FOA-2021-2320]en_US
dc.description.sponsorshipThe authors thank the Inoenue University Faculty of Science Department of Chemistry for the spectroscopy data and characterization of compounds. The authors also thank Esin Aki Yalcin and the research group for technical assistance. This study was financially supported by Inonu University Research Fund (Project Code: FBG-2021-2525 and FOA-2021-2320).en_US
dc.identifier.doi10.1007/s11030-022-10578-3
dc.identifier.endpage2787en_US
dc.identifier.issn1381-1991
dc.identifier.issn1573-501X
dc.identifier.issue6en_US
dc.identifier.pmid36508118en_US
dc.identifier.scopus2-s2.0-85143703371en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage2767en_US
dc.identifier.urihttps://doi.org/10.1007/s11030-022-10578-3
dc.identifier.urihttps://hdl.handle.net/11616/101049
dc.identifier.volume27en_US
dc.identifier.wosWOS:000898457600001en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherSpringeren_US
dc.relation.ispartofMolecular Diversityen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectAcetylcholinesteraseen_US
dc.subjectAcetyl groupen_US
dc.subjectADMETen_US
dc.subjectCarbonic anhydraseen_US
dc.subjectImidazolium salten_US
dc.subjectMolecular dockingen_US
dc.titleAcetylphenyl-substituted imidazolium salts: synthesis, characterization, in silico studies and inhibitory properties against some metabolic enzymesen_US
dc.typeArticleen_US

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