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

Rajput, Vishal Kumar; Leffler, Hakon LU ; Nilsson, Ulf J and Mukhopadhyay, Balaram (2014) In Bioorganic & Medicinal Chemistry Letters 24(15). p.3516-3520
Abstract
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, -4N, -4C, -7, -8N, -9N, and 9C using a competitive fluorescence polarization assay. Selective compounds were identified against galectin-3, 7, 8N, and 9N with up to 40-fold affinity enhancements relative to methyl α-d-galactopyranoside due to the coumarylmethyl moieties.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Bioorganic & Medicinal Chemistry Letters
volume
24
issue
15
pages
3516 - 3520
publisher
Elsevier
external identifiers
  • pmid:24973029
  • wos:000339228700060
  • scopus:84904068607
ISSN
1090-2120
DOI
10.1016/j.bmcl.2014.05.063
language
English
LU publication?
yes
id
f4ccf7f1-c4f1-431a-8476-a9e7dd6c3a97 (old id 4523739)
alternative location
http://www.ncbi.nlm.nih.gov/pubmed/24973029?dopt=Abstract
date added to LUP
2014-07-08 11:25:13
date last changed
2017-01-01 03:38:25
@article{f4ccf7f1-c4f1-431a-8476-a9e7dd6c3a97,
  abstract     = {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, -4N, -4C, -7, -8N, -9N, and 9C using a competitive fluorescence polarization assay. Selective compounds were identified against galectin-3, 7, 8N, and 9N with up to 40-fold affinity enhancements relative to methyl α-d-galactopyranoside due to the coumarylmethyl moieties.},
  author       = {Rajput, Vishal Kumar and Leffler, Hakon and Nilsson, Ulf J and Mukhopadhyay, Balaram},
  issn         = {1090-2120},
  language     = {eng},
  number       = {15},
  pages        = {3516--3520},
  publisher    = {Elsevier},
  series       = {Bioorganic & Medicinal Chemistry Letters},
  title        = {Synthesis and evaluation of iminocoumaryl and coumaryl derivatized glycosides as galectin antagonists.},
  url          = {http://dx.doi.org/10.1016/j.bmcl.2014.05.063},
  volume       = {24},
  year         = {2014},
}