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3-(1,2,3-Triazol-1-yl)-1-thio-galactosides as small, efficient, and hydrolytically stable inhibitors of galectin-3

Salameh, Bader LU ; Leffler, Hakon LU and Nilsson, Ulf LU (2005) In Bioorganic & Medicinal Chemistry Letters 15(14). p.3344-3346
Abstract
Copper(I)-catalyzed addition of alkynes to methyl 3-azido-3-deoxy-1-thio-β-d-galactopyranoside afforded stable and structurally simple 3-deoxy-3-(1H-1,2,3-triazol-1-yl)-1-thio-galactosides carrying a panel of substituents at the triazole C4 in high yields. The 3-(1H-[1,2,3]-triazol-1-yl)-1-thio-galactoside collection synthesized contained inhibitors of the tumor- and inflammation-related galectin-3 with Kd values as low as 107 μM, which is as potent as the natural disaccharide inhibitors lactose and N-acetyllactosamine.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Bioorganic & Medicinal Chemistry Letters
volume
15
issue
14
pages
3344 - 3346
publisher
Elsevier
external identifiers
  • pmid:15963723
  • wos:000230337100004
  • scopus:20644448817
ISSN
1090-2120
DOI
10.1016/j.bmcl.2005.05.084
language
English
LU publication?
yes
id
8ddae8f1-cd91-4055-8302-269a3bca19f2 (old id 158711)
date added to LUP
2007-07-10 14:12:33
date last changed
2017-04-23 03:43:55
@article{8ddae8f1-cd91-4055-8302-269a3bca19f2,
  abstract     = {Copper(I)-catalyzed addition of alkynes to methyl 3-azido-3-deoxy-1-thio-β-d-galactopyranoside afforded stable and structurally simple 3-deoxy-3-(1H-1,2,3-triazol-1-yl)-1-thio-galactosides carrying a panel of substituents at the triazole C4 in high yields. The 3-(1H-[1,2,3]-triazol-1-yl)-1-thio-galactoside collection synthesized contained inhibitors of the tumor- and inflammation-related galectin-3 with Kd values as low as 107 μM, which is as potent as the natural disaccharide inhibitors lactose and N-acetyllactosamine.},
  author       = {Salameh, Bader and Leffler, Hakon and Nilsson, Ulf},
  issn         = {1090-2120},
  language     = {eng},
  number       = {14},
  pages        = {3344--3346},
  publisher    = {Elsevier},
  series       = {Bioorganic & Medicinal Chemistry Letters},
  title        = {3-(1,2,3-Triazol-1-yl)-1-thio-galactosides as small, efficient, and hydrolytically stable inhibitors of galectin-3},
  url          = {http://dx.doi.org/10.1016/j.bmcl.2005.05.084},
  volume       = {15},
  year         = {2005},
}