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Synthesis and evaluation of iminocoumaryl and coumaryl derivatized glycosides as galectin antagonists

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Author

Summary, in English

A collection of iminocoumarylmethyl glycoside derivatives have been prepared by copper-catalyzed multi-component reaction of carbohydrate propargyl derivatives, sulfonyl azides, and salicylaldehyde or o-hydroxy acetophenone. The method is simple, versatile to all three components, and exceptionally high yielding. The carbohydrate N-sulfonyl iminocoumarine hybrid molecules were evaluated for binding galectin-1, -2, -3, -4 N, -4C, -7, -8 N, -9 N, and 9C using a competitive fluorescence polarization assay. Selective compounds were identified against galectin-3, 7, 8 N, and 9 N with up to 40-fold affinity enhancements relative to methyl α-d-galactopyranoside due to the coumarylmethyl moieties.

Publishing year

2014

Language

English

Pages

3516-3520

Publication/Series

Bioorganic & Medicinal Chemistry Letters

Volume

24

Issue

15

Document type

Journal article

Publisher

Elsevier

Topic

  • Microbiology in the medical area
  • Immunology in the medical area

Keywords

  • Antagonist
  • Coumarine
  • Galectin
  • Iminocoumarine
  • Multicomponent reaction

Status

Published

ISBN/ISSN/Other

  • ISSN: 0960-894X