Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1372813 | Bioorganic & Medicinal Chemistry Letters | 2008 | 5 Pages |
Abstract
The synthesis of carbohydrate-based glycogen phosphorylase inhibitors is attractive for potential applications in the treatment of type 2 diabetes. A titanium-mediated synthesis led to a benzoylated C-glucosylated cyclopropylamine intermediate, which underwent a benzoyl migration to afford the corresponding 2-hydroxy-C-glycoside. X-ray crystallographic studies revealed a unit cell composed of four molecules as pairs of dimers connected through two hydrogen bonds. The deprotection of the benzoate esters under Zemplén conditions afforded a glycogen phosphorylase inhibitor candidate displaying weak inhibition toward glycogen phosphorylase (16% at 2.5 mM).
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Philippe Bertus, Jan Szymoniak, Erwann Jeanneau, Tibor Docsa, Pál Gergely, Jean-Pierre Praly, Sébastien Vidal,