Synthesis of furo[2,3-c]carbazoles as potent α-glucosidase and α-amylase inhibitors

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dc.authorid0000-0002-3909-0694en_US
dc.authorid0000-0002-8325-8116en_US
dc.contributor.authorUçar, Tuğçe N. Uslu
dc.contributor.authorBingül, Murat
dc.contributor.authorŞahin, Hasan
dc.contributor.authorKandemir, Hakan
dc.contributor.authorŞengül, İbrahim Fazıl
dc.date.accessioned2024-11-05T12:58:55Z
dc.date.available2024-11-05T12:58:55Z
dc.date.issued2024en_US
dc.departmentDicle Üniversitesi, Eczacılık Fakültesi, Temel Eczacılık Bilimleri Bölümüen_US
dc.description.abstractThe carbazole-3-carbaldehyde 2, produced by N-ethyl carbazole via Vilsmeier-Haack reaction, was subjected to Dakin type oxidation with H2O2 and H2SO4 in methanol to produce the carbazole-3-ol 3. The reaction of 3 with a range of commercially available α-haloketones 4a–f in the presence of Al2O3 as catalyst in xylene led to their regio-selective cyclization to afford the furo[2,3-c]carbazoles 5a–f. Identification of the furo[2,3-c]carbazoles 5a–f were performed through 1H NMR,13C NMR, FT-IR and high resolution mass spectrometry. Single crystal X-ray diffraction analysis was employed to further confirm the structures of the some of the targeted compounds. In vitro antidiabetic activities of the newly synthesized furocarbazoles 5a–e were investigated utilizing α-glucosidase and α-amylase enzymes. The biological evaluation revealed the obvious efficiencies of the targeted molecules toward the α-glucosidase enzyme inhibition with the potent IC50 values compared to the standard acarbose. In the case of α-glucosidase inhibition, the furo[2,3-c]carbazoles chloro substituted 5c and nitro substituted 5f were found to be more potent than acarbose with the values of 215.0 and 162.70 μM, respectively. On the other hand, the compound 5f was found to be only promising candidate for α-amylase enzyme but not as effective as the standard acarbose.en_US
dc.description.sponsorshipResearch Found of the Tekirdag Namimath;k Kemal University NKUBAP.01.GA.23.475en_US
dc.identifier.citationUçar, T. N. U., Bingül, M., Şahin, H., Kandemir, H. ve Şengül, İ. F. (2024). Synthesis of furo[2,3-c]carbazoles as potent α-glucosidase and α-amylase inhibitors. Synthetic Communications, 54(19), 1698-1706.en_US
dc.identifier.endpage1706en_US
dc.identifier.issn0039-7911
dc.identifier.issue19en_US
dc.identifier.scopus2-s2.0-85203539034
dc.identifier.scopusqualityQ2
dc.identifier.startpage1698en_US
dc.identifier.urihttps://www.tandfonline.com/doi/full/10.1080/00397911.2024.2401628
dc.identifier.urihttps://hdl.handle.net/11468/28912
dc.identifier.volume54en_US
dc.identifier.wosWOS:001310411400001
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorBingül, Murat
dc.institutionauthorŞahin, Hasan
dc.language.isoenen_US
dc.publisherTaylor and Francis Ltd.en_US
dc.relation.ispartofSynthetic Communications
dc.relation.isversionof10.1080/00397911.2024.2401628en_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectCarbazoleen_US
dc.subjectFuranen_US
dc.subjectα-amylaseen_US
dc.subjectα-glucosidaseen_US
dc.titleSynthesis of furo[2,3-c]carbazoles as potent α-glucosidase and α-amylase inhibitorsen_US
dc.titleSynthesis of furo[2,3-c]carbazoles as potent ?-glucosidase and ?-amylase inhibitors
dc.typeArticleen_US

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