Synthesis, in vitro and in silico evaluation of indole linked carbohydrazides and 1,3,4-oxadiazoles as new α-glycosidase inhibitors

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dc.contributor.authorKocaman, Kubra
dc.contributor.authorBingul, Murat
dc.contributor.authorCeyhan, Sadik M.
dc.contributor.authorSahin, Hasan
dc.contributor.authorSaglam, Mehmet F.
dc.contributor.authorKandemir, Hakan
dc.contributor.authorSengul, Ibrahim F.
dc.date.accessioned2025-04-06T12:23:52Z
dc.date.available2025-04-06T12:23:52Z
dc.date.issued2025
dc.departmentTekirdağ Namık Kemal Üniversitesi
dc.description.abstractThe Hemetsberger indole reaction afforded 6-methyl and methoxy substituted indole-2-carboxylates 8 which were then reacted with an excess of hydrazine hydrate in ethanol to produce indole-2-carbohydrazides 9. Treatment of the compounds 9 with a range of commercially available benzoyl chlorides generated new indole linked diacyl hydrazines 10-15 and the corresponding cyclodehydration reaction in the presence of N,N-diisopropylethylamine (DIPEA) and p-toluenesulfonyl chloride (p-TsCl) in acetonitrile gave the targeted indole linked 1,3,4-oxadiazoles 16-21. The antidiabetic properties of the newly synthesized compounds were evaluated by employing alpha-glycosidase and alpha-amylase enzyme inhibition assays and the targeted compounds showed a range of inhibitory activities against alpha-glycosidase and alpha-amylase. The study revealed that the compounds selectively inhibit alpha-glycosidase enzyme. The detection of selective inhibition behaviours for alpha-glycosidase enzyme increased the novelty of the study and most of the IC50 values against the designated enzyme were found to be better than the standard acarbose. The structure-activity relation study illustrated that the oxadiazole ring with the methyl substituted indole and nitro substituted benzene rings demonstrated the best inhibition towards the alpha-glycosidase enzyme. The detected IC50 value for the identified compound 21 was found to be better (>25-fold) than the standard acarbose.
dc.description.sponsorshipResearch Found of the Tekirdag Namimath;k Kemal University [NKUBAP.01.GA.23.530]; Research Found of the Gebze Technical University [2023-A105-13]
dc.description.sponsorshipThis work has been supported by Research Found of the Tekirdag Nam & imath;k Kemal University (Project Number: NKUBAP.01.GA.23.530) and Research Found of the Gebze Technical University (Project Number: 2023-A105-13) .
dc.identifier.doi10.1016/j.molstruc.2024.141057
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85211704822
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2024.141057
dc.identifier.urihttps://hdl.handle.net/20.500.11776/17224
dc.identifier.volume1325
dc.identifier.wosWOS:001389216800001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250406
dc.subjectIndole
dc.subject4-oxadizole
dc.subjectCarbohydrazide
dc.subjectalpha-glycosidase
dc.subjectalpha-amylase
dc.subjectSelective inhibition
dc.titleSynthesis, in vitro and in silico evaluation of indole linked carbohydrazides and 1,3,4-oxadiazoles as new α-glycosidase inhibitors
dc.typeArticle

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