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Bioorg Med Chem. 2008 Aug 15;16(16):7811-23. doi: 10.1016/j.bmc.2008.06.044. Epub 2008 Jun 26.

Synthesis of stable and selective inhibitors of human galectins-1 and -3.

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1
Department of Chemistry, Université du Québec à Montréal, PO Box 8888, Succ. Centre-Ville, Montreal, Que., Canada H3C 3P8.

Abstract

The syntheses of glycolytically stable galactosides and lactosides have been made toward the selective inhibition of human galectins-1 and -3. Transition metal-catalyzed cross-coupling reactions were used to create carbon-carbon bond formation (Sonogashira, Suzuki, Heck, Glaser). Additionally, Hantzsch condensation was used to create novel 2-aminothiazoles which reacted with a panel of acylating and sulfonylating reagents. Moreover, dimeric galactosides and lactosides bearing triazoles, regiospecifically prepared using copper-catalyzed Huisgen azide-alkyne [1,3]-dipolar cycloaddition, provided efficient galectins-1 and -3 inhibitors. Best monovalent inhibitor among the tested series was (E)-methyl 2-phenyl-4-(beta-D-galactopyranosyl)-but-2-enoate 15 with inhibitory potency of 313 microM against galectin-1 and best dimers were bis-lactoside 68 and 75 having both inhibitory properties of 160 microM against Galectin-3.

PMID:
18674915
DOI:
10.1016/j.bmc.2008.06.044
[Indexed for MEDLINE]
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