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    Please use this identifier to cite or link to this item: http://tkuir.lib.tku.edu.tw:8080/dspace/handle/987654321/61753

    Title: Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors
    Authors: Shih, Tzenge-lien;Liang, Ming-tsung;Wu, Kuen-da;Lin, Chun-hung
    Contributors: 淡江大學化學學系
    Keywords: Azepane;d-(−)-Quinic acid;β-Galactosidase;Glycosidase inhibitor
    Date: 2011-02
    Issue Date: 2011-10-15 23:37:02 (UTC+8)
    Publisher: Oxford: Pergamon
    Abstract: An effective synthetic method for polyhydroxylated azepanes that contain an alkyl group (Me or Bu) at either the 7- or N-positions is developed. The synthetic routes are accomplished in eight to ten steps from d-(−)-quinic acid. Among the compounds synthesized, the polyhydroxy 7-butyl azepane (compound 3), which possessed the R-configuration at C-7 position, is shown to give potent inhibition against β-galactosidase (IC50 = 3 μM). Preliminary biological data indicate that the length of alkyl groups along with the proper stereochemistry at the C-7 position is essential for acquiring extra binding affinity. Using similar synthetic routes, the polyhydroxy N-methyl and N-butyl azepanes are synthesized for the comparison of their biological activities.
    Relation: Carbohydrate Research 346(2), pp.183-190
    DOI: 10.1016/j.carres.2010.11.014
    Appears in Collections:[Graduate Institute & Department of Chemistry] Journal Article

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