Salameh Bader A, Leffler Hakon, Nilsson Ulf J
Organic Chemistry, Lund University, PO Box 124, SE-221 00 Lund, Sweden.
Bioorg Med Chem Lett. 2005 Jul 15;15(14):3344-6. doi: 10.1016/j.bmcl.2005.05.084.
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.
在铜（I）催化下，炔烃与3-叠氮基-3-脱氧-1-硫代-β-D-吡喃半乳糖苷甲基酯发生加成反应，以高产率得到了结构稳定且简单的3-脱氧-3-（1H-1,2,3-三唑-1-基）-1-硫代半乳糖苷，其在三唑C4位带有一系列取代基。所合成的3-（1H-[1,2,3]-三唑-1-基）-1-硫代半乳糖苷库包含肿瘤和炎症相关的半乳糖凝集素-3的抑制剂，其解离常数（Kd）低至107微摩尔，与天然二糖抑制剂乳糖和N-乙酰乳糖胺的活性相当。
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