Effective ?-glycosidase inhibitors based on polyphenolic benzothiazole heterocycles

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dc.authorid0000-0002-7935-3954
dc.authorid0000-0001-7939-5380
dc.contributor.authorSevimli, Esra
dc.contributor.authorSeyhan, Gokce
dc.contributor.authorAkkaya, Didem
dc.contributor.authorSari, Suat
dc.contributor.authorBarut, Burak
dc.contributor.authorKoksoy, Baybars
dc.date.accessioned2026-02-08T15:15:08Z
dc.date.available2026-02-08T15:15:08Z
dc.date.issued2024
dc.departmentBursa Teknik Üniversitesi
dc.description.abstractalpha-Glycosidase inhibition is one of the main approaches to treat Diabetes mellitus. Polyphenolic moieties are known to be responsible for yielding exhibit potent alpha-glycosidase inhibitory effects. In addition, compounds containing benzothiazole and Schiff base functionalities were previously reported to show alpha-glycosidase inhibition. In this paper, the synthesis of seven new phloroglucinol-containing benzothiazole Schiff base derivatives through the reaction of 6-substituted-2-aminobenzothiazole compounds with 2,4,6-trihydroxybenzaldehyde using acetic acid as a catalyst was reported. The synthesized compounds were characterized using spectroscopic methods such as FT-IR, 1 H NMR, 13 C NMR, and elemental analysis. The synthesized compounds were evaluated for their inhibitory effects on alpha-glycosidase, compounds 3f and 3g were found to show significant inhibitory properties when compared to the positive control. The IC 50 values of 3f and 3g were calculated as 24.05 +/- 2.28 and 18.51 +/- 1.19 mu M, respectively. Kinetic studies revealed that compounds 3f and 3g exhibited uncompetitive mode of inhibition against alpha-glycosidase. Molecular modeling predicted druglikeness for the title compounds and underpinned the importance of phloroglucinol hydroxyls for interacting with the key residues of alpha-glycosidase.
dc.identifier.doi10.1016/j.bioorg.2024.107366
dc.identifier.issn0045-2068
dc.identifier.issn1090-2120
dc.identifier.pmid38636435
dc.identifier.scopus2-s2.0-85190525313
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.bioorg.2024.107366
dc.identifier.urihttps://hdl.handle.net/20.500.12885/5629
dc.identifier.volume147
dc.identifier.wosWOS:001231203900001
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherAcademic Press Inc Elsevier Science
dc.relation.ispartofBioorganic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzWOS_KA_20260207
dc.subjectBenzothiazole
dc.subjectEnzyme inhibition
dc.subjectalpha-glycosidase
dc.subjectSchiff base
dc.titleEffective ?-glycosidase inhibitors based on polyphenolic benzothiazole heterocycles
dc.typeArticle

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