Kocaman, KubraBingul, MuratCeyhan, Sadik M.Sahin, HasanSaglam, Mehmet F.Kandemir, HakanSengul, Ibrahim F.2025-02-222025-02-2220250022-28601872-8014https://doi.org/10.1016/j.molstruc.2024.141057https://hdl.handle.net/11468/29749The 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.eninfo:eu-repo/semantics/closedAccessIndole4-oxadizoleCarbohydrazidealpha-glycosidasealpha-amylaseSelective inhibitionArticle1325WOS:0013892168000012-s2.0-8521170482210.1016/j.molstruc.2024.141057Q1Q2