Journal
TETRAHEDRON LETTERS
Volume 50, Issue 29, Pages 4254-4257Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.04.134
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canadian Research Chair in Therapeutic Chemistry
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A catalytic synthesis of novel 4-linked C-glycosyl coumarins was achieved using a domino Heck reaction/lactonization process. Methyl 3-glycosyl cinnamates were prepared from methyl 4-glycosyl-but-2-enoates using a panel of aryl iodides under Heck conditions. A direct application of this new methodology was made toward preliminary hemagglutination inhibition assays against galectins-1 and -3. C-Galactoside 30 had an IC50 of 313 mu M against galectin-1. (C) 2009 Elsevier Ltd. All rights reserved.
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