1,3-Dipolar cycloaddition reactions on carbohydrate-based templates: synthesis of spiro-isoxazolines and 1,2,4-oxadiazoles as glycogen phosphorylase inhibitors |
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Authors: | Mahmoud Benltifa Sébastien Vidal Peter G Goekjian Jean-Pierre Praly |
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Institution: | a Laboratoire de Chimie Organique 2 - Glycochimie, Université Claude Bernard Lyon 1, UMR-CNRS 5181, CPE-Lyon, Bâtiment 308, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France b Laboratoire de Synthèse Hétérocyclique, Photochimie et Complexation, Faculté des Sciences de Monastir, Avenue de l’Environnement, 5000 Monastir, Tunisia |
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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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Keywords: | 1 3-Dipolar cycloadditions Glycals Spiro-isoxazolines 1 2 4-Oxadiazoles |
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