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

Bader A Salameh; Hakon Leffler; Ulf J Nilsson

doi:10.1016/j.bmcl.2005.05.084

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

Bioorg Med Chem Lett. 2005 Jul 15;15(14):3344-6. doi: 10.1016/j.bmcl.2005.05.084.

Authors

Bader A Salameh¹, Hakon Leffler, Ulf J Nilsson

Affiliation

¹ Organic Chemistry, Lund University, PO Box 124, SE-221 00 Lund, Sweden.

PMID: 15963723
DOI: 10.1016/j.bmcl.2005.05.084

Abstract

Copper(I)-catalyzed addition of alkynes to methyl 3-azido-3-deoxy-1-thio-beta-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 microM, which is as potent as the natural disaccharide inhibitors lactose and N-acetyllactosamine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Copper / chemistry
Drug Design
Galactosides / chemical synthesis
Galactosides / classification
Galactosides / pharmacology*
Galectin 3 / antagonists & inhibitors*
Hydrolysis
Molecular Conformation
Structure-Activity Relationship

Substances

Galactosides
Galectin 3
Copper