Synthesis and evaluation of iminocoumaryl and coumaryl derivatized glycosides as galectin antagonists
Författare
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.
Avdelning/ar
Publiceringsår
2014
Språk
Engelska
Sidor
3516-3520
Publikation/Tidskrift/Serie
Bioorganic & Medicinal Chemistry Letters
Volym
24
Issue
15
Dokumenttyp
Artikel i tidskrift
Förlag
Elsevier
Ämne
- Microbiology in the medical area
- Immunology in the medical area
Nyckelord
- Antagonist
- Coumarine
- Galectin
- Iminocoumarine
- Multicomponent reaction
Status
Published
ISBN/ISSN/Övrigt
- ISSN: 0960-894X