Synthesis of N-(beta-D-glucopyranosyl) monoamides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase |
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Authors: | Czifrák Katalin Hadady Zsuzsa Docsa Tibor Gergely Pál Schmidt Jürgen Wessjohann Ludger Somsák László |
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Affiliation: | Department of Organic Chemistry, Faculty of Science, University of Debrecen, PO Box 20, H-4010 Debrecen, Hungary. |
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Abstract: | O-peracetylated N-(beta-D-glucopyranosyl)imino trimethylphosphorane obtained in situ from 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide and PMe3 was reacted with saturated and unsaturated aliphatic and aromatic dicarboxylic acids, or their anhydrides, or monoesters to give the corresponding N-(beta-D-glucopyranosyl) monoamides of dicarboxylic acids or derivatives. The acetyl protecting groups were removed according to the Zemplén protocol to give a series of compounds which showed moderate inhibitory effects against rabbit muscle glycogen phosphorylase b. The best inhibitor was 3-(N-beta-D-glucopyranosyl-carbamoyl)propanoic acid (7) with Ki = 20 microM. |
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Keywords: | N-Glycosylamides Glucose analogues Inhibitors Glycogen phosphorylase |
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