Iminosugars Spiro-Linked with Morpholine-Fused 1,2,3-Triazole: Synthesis, Conformational Analysis, Glycosidase Inhibitory Activity, Antifungal Assay, and Docking Studies.

ABSTRACT: Synthesis of iminosugars 1, 2, 3a, and 4a and N-alkyl (ethyl, butyl, hexyl, octyl, decyl, and dodecyl) derivatives 3b-g and 4b-g spiro-linked with morpholine-fused 1,2,3-triazole is described. Conformation of the piperidine ring in each spiro-iminosugar was evaluated by ¹H NMR spectroscopy, and conformational change in N-alkylated compounds 4b-g with respect to parent spiro-iminosugar 4a is supported by density functional theory calculations. Out of 16 new spiro-iminosugars, the spiro-iminosugars 3a (IC₅₀ = 0.075 μM) and 4a (IC₅₀ = 0.036 μM) were found to be more potent inhibitors of α-glucosidase than the marketed drug miglitol (IC₅₀ = 0.100 μM). In additi

SUBMITTER: Chavan SR 

PROVIDER: S-EPMC6044920 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature