Pentafluorobenzyl-substituted benzimidazolium salts: Synthesis, characterization, crystal structures, computational studies and inhibitory properties of some metabolic enzymes

Basit Öğe Kaydı
dc.authoridDemir, Yeliz/0000-0003-3216-1098
dc.authoridGulcin, ilhami/0000-0001-5993-1668
dc.authoridAktaş, Aydın/0000-0001-8496-6782
dc.authoridTASKIN TOK, Tugba/0000-0002-0064-8400
dc.authoridHAMIDE, Mahmut/0000-0001-7507-5603
dc.authoridHAMIDE, Mahmut/0000-0002-9347-7697
dc.authorwosidDemir, Yeliz/ABI-5719-2020
dc.authorwosidGulcin, ilhami/F-1428-2014
dc.authorwosidGüzel, Bilgehan/D-1464-2018
dc.authorwosidAktaş, Aydın/J-6194-2019
dc.authorwosidTASKIN TOK, Tugba/A-8885-2016
dc.contributor.authorHamide, Mahmut
dc.contributor.authorGok, Yetkin
dc.contributor.authorDemir, Yeliz
dc.contributor.authorYakali, Gul
dc.contributor.authorTok, Tugba Taskin
dc.contributor.authorAktas, Aydin
dc.contributor.authorSevincek, Resul
dc.date.accessioned2024-08-04T20:52:03Z
dc.date.available2024-08-04T20:52:03Z
dc.date.issued2022
dc.departmentİnönü Üniversitesien_US
dc.description.abstractThis work contains the synthesis and characterization of the pentafluorobenzyl-substituted benzimidazolium salts which N -heterocyclic carbene (NHC) precursors. All compounds were characterized by using 1 H, 13 C, and 19 F NMR, FT-IR spectroscopy, and elemental analysis techniques. All the spectroscopy and elemental analysis data fully confirm the proposed formulas. In the synthesized compounds, the molecular structures of compounds 1-(2-methylbenzyl)-3-(2,3,4,5,6-pentafluorobenzyl)benzimidazolium bromide ( 1b ), 1-(4-methylbenzyl)-3-(2,3,4,5,6-pentafluorobenzyl)benzimidazolium bromide ( 1d ) and 1-(4-trifluoromethylbenzyl)-3-(2,3,4,5,6-pentafluorobenzyl)benzimidazolium bromide ( 1f ) were enlightened by single crystal X-ray diffraction studies. After enzyme inhibition study, a new series of pentafluorobenzyl-substituted NHC precursors were determined to be highly potent inhibitors for acetylcholinesterase (AChE) enzyme and carbonic anhydrases (hCAs) isoenzymes. K i values were found in the range of 7.20 +/- 1.31 to 28.26 +/- 5.72 nM for AChE , 10.25 +/- 0.93 to 40.93 +/- 3.89 nM toward hCA I as pervasive metal containing enzymes present in prokaryotes and eukaryotes, and 3.33 +/- 0.15 to 58.22 +/- 6.99 nM for hCA II as the key enzyme promising strategy for the treatment of neurological disorders such as Alzheimer's disease. The molecular docking study performed for compounds had higher potential inhibitory properties involved in a novel series of pentafluorobenzyl-substituted NHC precursors based on the binding energy and interaction types against AChE and hCAs. (c) 2022 Elsevier B.V. All rights reserved.en_US
dc.description.sponsorshipDokuz Eyluel University [2010.KB.FEN.13]en_US
dc.description.sponsorshipThe authors acknowledge Dokuz Eyluel University for the use of the Oxford Rigaku Xcalibur Eos Diffractometer (purchased under University Research Grant No: 2010.KB.FEN.13). The authors thank Esin Aki Yalcin and the research group for technical assistance.en_US
dc.identifier.doi10.1016/j.molstruc.2022.133266
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85131350730en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2022.133266
dc.identifier.urihttps://hdl.handle.net/11616/100697
dc.identifier.volume1265en_US
dc.identifier.wosWOS:000814696400008en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevieren_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.subjectAcetylcholinesteraseen_US
dc.subjectCarbonic anhydraseen_US
dc.subjectMolecular dockingen_US
dc.subjectN-heterocyclic carbenesen_US
dc.subjectPentafluorobenzylen_US
dc.subjectX-ray diffractionen_US
dc.titlePentafluorobenzyl-substituted benzimidazolium salts: Synthesis, characterization, crystal structures, computational studies and inhibitory properties of some metabolic enzymesen_US
dc.typeArticleen_US

Dosyalar

Koleksiyon

WoS İndeksli Yayınlar Koleksiyonu
Scopus İndeksli Yayınlar Koleksiyonu