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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. LU 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, -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.

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author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Antagonist, Coumarine, Galectin, Iminocoumarine, Multicomponent reaction
in
Bioorganic & Medicinal Chemistry Letters
volume
24
issue
15
pages
5 pages
publisher
Elsevier
external identifiers
  • pmid:24973029
  • wos:000339228700060
  • scopus:84904068607
  • pmid:24973029
ISSN
0960-894X
DOI
10.1016/j.bmcl.2014.05.063
language
English
LU publication?
yes
id
f4ccf7f1-c4f1-431a-8476-a9e7dd6c3a97 (old id 4523739)
date added to LUP
2016-04-01 10:29:27
date last changed
2023-02-08 07:42:22
@article{f4ccf7f1-c4f1-431a-8476-a9e7dd6c3a97,
  abstract     = {{<p>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.</p>}},
  author       = {{Rajput, Vishal Kumar and Leffler, Hakon and Nilsson, Ulf J. and Mukhopadhyay, Balaram}},
  issn         = {{0960-894X}},
  keywords     = {{Antagonist; Coumarine; Galectin; Iminocoumarine; Multicomponent reaction}},
  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}},
  doi          = {{10.1016/j.bmcl.2014.05.063}},
  volume       = {{24}},
  year         = {{2014}},
}