1,3-Dipolar cycloaddition reactions on carbohydrate-based templates: synthesis of spiro-isoxazolines and 1,2,4-oxadiazoles as glycogen phosphorylase inhibitors

被引：89

作者：

Benltifa, Mahmoud

Vidal, Sebastien

Gueyrard, David

Goekjian, Peter G.

Msaddek, Moncef

Praly, Jean-Pierre

机构：

[1] Univ Lyon 1, Lab Chim Organ 2, UMR 5181, CNRS,CPE Lyon, F-69622 Villeurbanne, France

[2] Fac Sci Monastir, Lab Synthese Heterocycl Photochim & Complexat, Monastir 5000, Tunisia

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 34期

关键词：

1,3-dipolar cycloadditions; glycals; spiro-isoxazolines; 1,2,4-oxadiazoles;

D O I：

10.1016/j.tetlet.2006.06.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1, 3-Dipolar cycloaddition of aryl nitrile oxides to benzyl/acetyl-protected exo-glucals and to a benzoylated glucosyl cyanide led in high yield to spiro-isoxazolines and to 3-aryl-5-glucosyl-1,2,4-oxadiazoles, respectively. The choice of the protective groups was important to the outcome of the cycloaddition and for the deprotection of the adducts. Cleavage of the ester protecting groups (acetyl, benzoyl) provided water-soluble spiro-isoxazolines and 3-aryl-5-glucosyl-1,2,4-oxadiazoles, evaluated as glycogen phosphorylase inhibitors. Preliminary tests showed IC50 values in the mu M range. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：6143 / 6147

页数：5

共 30 条

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