Selenourea and thiourea derivatives of chiral and achiral enetetramines: Synthesis, characterization and enzyme inhibitory properties

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dc.authoridGulcin, ilhami/0000-0001-5993-1668
dc.authorscopusid57198017711
dc.authorscopusid57194874374
dc.authorscopusid57219208093
dc.authorscopusid6603437287
dc.authorscopusid7004373425
dc.authorscopusid7005334934
dc.authorscopusid56249121800
dc.authorwosidGulcin, ilhami/F-1428-2014
dc.contributor.authorYigit, Murat
dc.contributor.authorCelepci, Duygu Barut
dc.contributor.authorTaslimi, Parham
dc.contributor.authorYigit, Beyhan
dc.contributor.authorCetinkaya, Engin
dc.contributor.authorOzdemir, Ismail
dc.contributor.authorAygun, Muhittin
dc.date.accessioned2023-01-12T19:54:28Z
dc.date.available2023-01-12T19:54:28Z
dc.date.issued2022
dc.departmentN/A/Departmenten_US
dc.description.abstractA series of chiral and achiral cyclic seleno-and thiourea compounds bearing benzyl groups on N-atoms were prepared from enetetramines and appropriate Group VI elements in good yields. All the synthesized compounds were characterized by elemental analysis, FT-IR, H-1 NMR and C-13 NMR spectroscopy, and the molecular and crystal structures of (R,R)-4b and (R,R)-5b were confirmed by the single-crystal X-ray diffraction method. These assayed for their activities against metabolic enzymes acetylcholinesterase, butyrylcholinesterase, and alpha-glycosidase. These selenourea and thiourea derivatives of chiral and achiral enetetramines effectively inhibit AChE and BChE with IC50 values in the range of 3.32-11.36 and 1.47-9.73 mu M, respectively. Also, these compounds inhibited alpha-glycosidase enzyme with IC50 values varying between 1.37 and 8.53 mu M. The results indicated that all the synthesized compounds exhibited excellent inhibitory activities against mentioned enzymes as compared with standard inhibitors. Representatively, the most potent compound against alpha-glycosidase enzyme, (S,S)-5b, was 12-times more potent than standard inhibitor acarbose; 7b and 8a as most potent compounds against cholinesterase enzymes, were around 5 and 13-times more potent than standard inhibitor tacrine against achethylcholinesterase (AChE) and butyrylcholinesterase (BChE), respectively.en_US
dc.description.sponsorshipDokuz Eylul University [2010.KB.FEN.13]en_US
dc.description.sponsorshipThe authors thank Dokuz Eylul University for the use of the Oxford Rigaku Xcalibur Eos Diffractometer (purchased under University Research Grant No: 2010.KB.FEN.13).en_US
dc.identifier.doi10.1016/j.bioorg.2021.105566
dc.identifier.issn0045-2068
dc.identifier.issn1090-2120
dc.identifier.pmid34974209en_US
dc.identifier.scopus2-s2.0-85121986127en_US
dc.identifier.scopusqualityQ1en_US
dc.identifier.urihttps://doi.org/10.1016/j.bioorg.2021.105566
dc.identifier.urihttps://hdl.handle.net/11454/76434
dc.identifier.volume120en_US
dc.identifier.wosWOS:000788750000012en_US
dc.identifier.wosqualityQ1en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherAcademic Press Inc Elsevier Scienceen_US
dc.relation.ispartofBioorganic Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectChiral selenoureaen_US
dc.subjectThioureaen_US
dc.subjectEnetetramineen_US
dc.subjectCrystal structureen_US
dc.subjectEnzyme inhibitionen_US
dc.subjectAchethylcholinesteraseen_US
dc.subjectButyrylcholinesteraseen_US
dc.subjectN-Heterocyclic Carbeneen_US
dc.subjectAlpha-Glucosidase Inhibitorsen_US
dc.subjectElectron-Rich Olefinsen_US
dc.subjectCarbonic-Anhydraseen_US
dc.subjectCrystal-Structureen_US
dc.subjectBenzimidazole Derivativesen_US
dc.subjectVibrational Propertiesen_US
dc.subjectBiological Evaluationen_US
dc.subjectMetal-Complexesen_US
dc.subjectIn-Vitroen_US
dc.titleSelenourea and thiourea derivatives of chiral and achiral enetetramines: Synthesis, characterization and enzyme inhibitory propertiesen_US
dc.typeArticleen_US

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