Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 20, Issue 24, Pages 7529-7533Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2010.09.111
Keywords
Neuraminidase; Glycosidase; Inhibitor; CuAAC; Triazole; Sialic acid
Categories
Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Alberta Ingenuity Centre for Carbohydrate Sciences (AICCS)
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We report the synthesis of a series of C9 and N5Ac modified analogs of 2,3-didehydro-N-acetyl-neuraminic acid (DANA) and their inhibitory potency for the human neuraminidase 3 (NEU3) enzyme. We were able to generate a small library of compounds through the synthesis of azide derivatives of DANA, followed by Cu-catalyzed azide-alkyne cycloaddition (CuAAC) to generate triazole-containing inhibitors. Our results suggest that NEU3 can tolerate large hydrophobic groups at the C9 position; however, none of the derivatives made at the N5Ac side-chain were active. We identify three new inhibitors that have comparable potency to the best reported inhibitors of the enzyme. (C) 2010 Elsevier Ltd. All rights reserved.
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