Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5278623 | Tetrahedron Letters | 2006 | 5 Pages |
Abstract
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 μM range.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Mahmoud Benltifa, Sébastien Vidal, David Gueyrard, Peter G. Goekjian, Moncef Msaddek, Jean-Pierre Praly,