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

Summary, in English

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: Bader Salameh; Hakon Leffler; Ulf Nilsson
• Department/s: Centre for Analysis and Synthesis; Division of Microbiology, Immunology and Glycobiology - MIG
• Publishing year: 2005
• Language: English
• Pages: 3344-3346
• Publication/Series: Bioorganic & Medicinal Chemistry Letters
• Volume: 15
• Issue: 14
• Links: http://dx.doi.org/10.1016/j.bmcl.2005.05.084
• Document type: Journal article
• Publisher: Elsevier
• Topic: Organic Chemistry
• Status: Published
• ISBN/ISSN/Other: ISSN: 0960-894X