Synthesis of N-(β-D-glucopyranosyl) monoarnides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase

被引：20

作者：

Czifrak, Katalin

Hadady, Zsuzsa

Doesa, Tibor

Gergely, Pal

Schmidt, Juergen

Wessjohann, Ludger

Somsak, Laszlo

机构：

[1] Univ Debrecen, Fac Sci, Dept Organ Chem, H-4010 Debrecen, Hungary

[2] Univ Debrecen, Signalling & Apoptosis Res Grp Hungarian, Acad Sci, Res Ctr Mol Med, H-4012 Debrecen, Hungary

[3] Univ Debrecen, Med & Hlth Sci Ctr, Dept Med Chem, H-4012 Debrecen, Hungary

[4] Leibniz Inst Plant Biochem, Dept Bioorgan Chem, D-06120 Halle, Saale, Germany

来源：

CARBOHYDRATE RESEARCH | 2006年 / 341卷 / 08期

基金：

匈牙利科学研究基金会;

关键词：

N-glycosylamides; glucose analogues; inhibitors; glycogen phosphorylase;

D O I：

10.1016/j.carres.2006.03.002

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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 Zemplen 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-carbamoy)propanoic acid (7) with K-i = 20 mu M. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：947 / 956

页数：10

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