Synthesis and structure-activity relationships of C-glycosylated oxadiazoles as inhibitors of glycogen phosphorylase

被引：64

作者：

Toth, Marietta ^{[1
]}

Kun, Sandor ^{[1
]}

Bokor, Eva ^{[1
]}

Benltifa, Mahmoud ^{[2
,3
,4
]}

Tallec, Gaylord ^{[2
,3
,4
]}

Vidal, Sebastien ^{[2
,3
,4
]}

Docsa, Tibor ^{[5
]}

Gergely, Pal ^{[6
]}

Somsak, Laszlo ^{[1
]}

Praly, Jean-Pierre ^{[2
,3
,4
]}

机构：

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

[2] Univ Lyon, Inst Chim & Biochim Mol & Supramol, CNRS, Lab Chim Organ 2,UMR 5246, F-69622 Villeurbanne, France

[3] Univ Lyon 1, F-69622 Villeurbanne, France

[4] CPE Lyon, F-69616 Villeurbanne, France

[5] Univ Debrecen, Cell Biol & Signaling Res Grp, Hungarian Acad Sci, Dept Med Chem,Med & Hlth Sci Ctr, H-4032 Debrecen, Hungary

[6] Univ Debrecen, Dept Med Chem, Med & Hlth Sci Ctr, H-4032 Debrecen, Hungary

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2009年 / 17卷 / 13期

基金：

匈牙利科学研究基金会;

关键词：

C-Glycosyl compounds; 1,3,4-Oxadiazoles; 1,2,4-Oxadiazoles; Glycogen phosphorylase; Inhibitors; TYPE-2; DIABETES-MELLITUS; 2,5-DISUBSTITUTED 1,3,4-OXADIAZOLES; ANTIDIABETIC AGENTS; EVOLVING EPIDEMIC; TARGETS; BINDING; MUSCLE; CYANIDES; THERAPY; AMIDES;

D O I：

10.1016/j.bmc.2009.04.036

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：

A series of per-O-benzoylated 5-beta-D-glucopyranosyl-2-substituted-1,3,4-oxadiazoles was prepared by acylation of the corresponding 5-(beta-D-glucopyranosyl) tetrazole. As an alternative, oxidation of 2,6-anhydro-aldose benzoylhydrazones by iodobenzene I, I-diacetate afforded the same oxadiazoles. 1,3-Dipolar cycloaddition of nitrile oxides to per-O-benzoylated beta-D-glucopyranosyl cyanide gave the corresponding 5-beta-D-glucopyranosyl-3-substituted-1,2,4-oxadiazoles. The O-benzoyl protecting groups were removed by base-catalyzed transesterification. The 1,3,4-oxadiazoles were practically inefficient as inhibitors of rabbit muscle glycogen phosphorylase b while the 1,2,4-oxadiazoles displayed inhibitory activities in the micromolar range. The best inhibitors were the 5-beta-D-glucopyranosyl-3-(4-methylphenyl-and -2-naphthyl)- 1,2,4-oxadiazoles (K-i = 8.8 and 11.6 mu M, respectively). A detailed analysis of the structure-activity relationships is presented. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：4773 / 4785

页数：13

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