Synthesis of new carboxylates and sulfonates containing thiazolidin-4-one ring and evaluation of inhibitory properties against some metabolic enzymes

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dc.authoridKarakus, Ahmet/0000-0003-1458-808X
dc.authoridTaslimi, Parham/0000-0002-3171-0633
dc.authoridSadeghian, nastaran/0009-0004-2966-9231
dc.contributor.authorTokali, Feyzi Sinan
dc.contributor.authorTaslimi, Parham
dc.contributor.authorTuzun, Burak
dc.contributor.authorKarakus, Ahmet
dc.contributor.authorSadeghian, Nastaran
dc.contributor.authorGulcin, Ilhami
dc.date.accessioned2024-10-26T18:09:41Z
dc.date.available2024-10-26T18:09:41Z
dc.date.issued2023
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractA series of thizaolidin-4-one derivatives (3a-o) was synthesized with excellent yield (94-97%) and the structures of the compounds were characterized with Fourier-transform Infrared (FTIR), Nuclear Magnetic Resonance (H-1 NMR-C-13 NMR), and High-resolution Mass Spectroscopy (HRMS). Novel compounds were tested towards some metabolic enzymes including acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human carbonic anhydrase I-II (hCA I-II). All the synthetic analogs had potent inhibitory strength with Ki values in the range of 161.28 +/- 16.91-943.13 +/- 57.23nM against hCA-I and 151.77 +/- 21.42-879.89 +/- 57.70 nM against hCA-II in comparison to the standard acetazolamide K-i = 847.18 +/- 75.41nM (for hCA-I) and Ki = 776.12 +/- 70.62nM (for hCA-II). Most of the compounds showed potent inhibitory activity against AChE and BChE enzymes with IC50 value 823.71-984.32 nM, 321.88-879.02 nM, 2.61-83.08 nM compared to the standard compounds (928.85, 691.41, and 68.85 nM), respectively. Additionally, the molecular docking study was carried out for the most active compound for the determination of ligand-enzyme interactions. Also, the Absorption, Distribution, Metabolism, Excretion and Toxicity (ADME/T) properties of the molecules were calculated. [GRAPHICS] .
dc.description.sponsorshipResearch Fund of Bartin University [2021-FEN-B-009]; Sivas Cumhuriyet University [RGD-020]
dc.description.sponsorshipThis work was supported by the Research Fund of Bartin University with the project number 2021-FEN-B-009 and Sivas Cumhuriyet University with the project number RGD-020. The numerical calculations reported in this paper were fully/partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).
dc.identifier.doi10.1007/s13738-023-02861-3
dc.identifier.endpage2642
dc.identifier.issn1735-207X
dc.identifier.issn1735-2428
dc.identifier.issue10
dc.identifier.scopus2-s2.0-85167356789
dc.identifier.scopusqualityQ3
dc.identifier.startpage2631
dc.identifier.urihttps://doi.org/10.1007/s13738-023-02861-3
dc.identifier.urihttps://hdl.handle.net/20.500.12418/30229
dc.identifier.volume20
dc.identifier.wosWOS:001045107700001
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSpringer
dc.relation.ispartofJournal of the Iranian Chemical Society
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectThizaolidin-4-one
dc.subjectSynthesis
dc.subjectEnzyme inhibition
dc.subjectMolecular docking
dc.subjectADME/T
dc.titleSynthesis of new carboxylates and sulfonates containing thiazolidin-4-one ring and evaluation of inhibitory properties against some metabolic enzymes
dc.typeArticle

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