Synthesis of indole-2-carbohydrazides and 2-(indol-2-yl)-1,3,4-oxadiazoles as antioxidants and their acetylcholinesterase inhibition properties

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dc.contributor.authorBingul, Murat
dc.contributor.authorSaglam, Mehmet F.
dc.contributor.authorKandemir, Hakan
dc.contributor.authorBoga, Mehmet
dc.contributor.authorSengul, Ibrahim F.
dc.date.accessioned2024-04-24T16:01:57Z
dc.date.available2024-04-24T16:01:57Z
dc.date.issued2019
dc.departmentDicle Üniversitesien_US
dc.description.abstractA range of novel 4,6-dimethoxy-1H-indole-2-carbohydrazides was prepared starting from methyl 4,6-dimethoxy-1H-indole-2-carboxylate which underwent cyclodehydration to generate the corresponding 2-(indol-2-yl)-1,3,4-oxadiazole scaffolds in the presence of N,N-diisopropylethylamine and p-toluenesulfonyl chloride in acetonitrile. All novel compounds were fully characterized by H-1 NMR, C-13 NMR, FT-IR, and high-resolution mass spectroscopic data. Biological importance of the designated compounds was identified by employing three different antioxidant property determination assays, namely DPPH free radical scavenging, ABTS cationic radical decolarization, and cupric reducing antioxidant capacity (CUPRAC). The anticholinesterase properties were also evaluated by the acetylcholinesterase and butyrylcholinesterase enzyme inhibition assays. According to the results, the indole compounds possessing carbohydrazide functionality were found to be more promising antioxidant targets than the 2-(indol-2-yl)-1,3,4-oxadiazole systems. N'-Benzoyl-4,6-dimethoxy-1H-indole-2-carbohydrazide, a member of the dimethoxyindole-2-carbohydrazide group, demonstrated a better inhibition performance than the standards. Additionally, extremely important results were obtained in the anticholinesterase enzyme inhibition assays in the case of 2-(indol-2-yl)-1,3,4-oxadiazole derivatives. [GRAPHICS] .en_US
dc.description.sponsorshipGebze Technical University; Dicle Universityen_US
dc.description.sponsorshipWe gratefully acknowledge the financial support for this research from Gebze Technical University and Dicle University.en_US
dc.identifier.doi10.1007/s00706-019-02462-y
dc.identifier.endpage1560en_US
dc.identifier.issn0026-9247
dc.identifier.issn1434-4475
dc.identifier.issue8en_US
dc.identifier.scopus2-s2.0-85069523959
dc.identifier.scopusqualityQ2
dc.identifier.startpage1553en_US
dc.identifier.urihttps://doi.org/10.1007/s00706-019-02462-y
dc.identifier.urihttps://hdl.handle.net/11468/14530
dc.identifier.volume150en_US
dc.identifier.wosWOS:000477624300018
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherSpringer Wienen_US
dc.relation.ispartofMonatshefte Fur Chemie
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectHeterocyclesen_US
dc.subjectBioorganic Chemistryen_US
dc.subjectEnzymes Inhibitionen_US
dc.subjectIndolesen_US
dc.titleSynthesis of indole-2-carbohydrazides and 2-(indol-2-yl)-1,3,4-oxadiazoles as antioxidants and their acetylcholinesterase inhibition propertiesen_US
dc.titleSynthesis of indole-2-carbohydrazides and 2-(indol-2-yl)-1,3,4-oxadiazoles as antioxidants and their acetylcholinesterase inhibition properties
dc.typeArticleen_US

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