Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 20, Issue 6, Pages 1957-1960Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2010.01.141
Keywords
Selectin inhibitors; sLe(x) Mimics; C-Glycosides; Fluorine
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Funding
- Ministere de l'Enseignement Superieur et de la Recherche
- Perigene Inc.
- Association pour la Recherche contre le Cancer
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The synthesis of fluorinated C-mannopeptides and their evaluation as E- and P-selectin inhibitors is described. These molecules are difluorinated analogues of CH2-glycopeptides already reported to act as sLe(x) mimics. The alpha and beta anomers of these CF2-glycopeptides have been prepared, as well as their 1-hydroxy analogues which were present in solution as an equilibrium mixture of alpha- and beta-pyranose and alpha- and beta-furanose forms. These molecules showed inhibitory activities comparable to their CH2 counterparts with a moderate influence of the pseudo-anomeric center configuration. (C) 2010 Elsevier Ltd. All rights reserved.
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