Synthesis of N-(β-D-glucopyranosyl)- and N-(2-acetamido-2-deoxy-β-D-glucopyranosyl) amides as inhibitors of glycogen phosphorylase

被引：62

作者：

Györgydeák, Z

Hadady, Z

Felföldi, N

Krakomperger, A

Nagy, V

Tóth, M

Brunyánszki, A

Docsa, T

Gergely, P

Somsák, L

机构：

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

[2] Med & Hlth Sci Ctr, Dept Med Chem, H-4026 Debrecen, Hungary

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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2004年 / 12卷 / 18期

基金：

匈牙利科学研究基金会;

关键词：

N-glycosylamides; inhibitors; glycogen phosphorylase;

D O I：

10.1016/j.bmc.2004.07.013

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：

2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl- and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl azides were transformed into the corresponding per-O-acetylated N-(beta-D-glycopyranosyl) amides via a PMe3 mediated Staudinger protocol (generation of N-(beta-D-glycopyranosyl)imino-trimethylphosphoranes followed by acylation with carboxylic acids, acid chlorides or anhydrides). The deprotected compounds obtained by Zemplen deacetylation were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. The best inhibitor of this series has been N-(beta-D-glucopyranosyl) 3-(2-naphthyl)-propenoic amide (K-i = 3.5 muM). (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4861 / 4870

页数：10

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