di(3-deoxy-3-(4-((butylamino)carbonyl)-1H-1,2,3-triazol-1-yl)-β-D-galactopyranosyl)sulfane | 1242965-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: di(3-deoxy-3-(4-((butylamino)carbonyl)-1H-1,2,3-triazol-1-yl)-β-D-galactopyranosyl)sulfane
• 英文别名: N-butyl-1-[(2S,3R,4S,5R,6R)-2-[(2S,3R,4S,5R,6R)-4-[4-(butylcarbamoyl)triazol-1-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]triazole-4-carboxamide
• CAS: 1242965-37-2
• 化学式: C₂₆H₄₂N₈O₁₀S
• 分子量: 658.733
• InChiKey: MVTBKMFCNHAEHU-YJYVSZKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  285
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  di(2,4,6-tri-O-acetyl-3-deoxy-3-(4-(methoxycarbonyl)-1H-1,2,3-triazol-1-yl)-β-D-galactopyranosyl)sulfane 、 正丁胺 在 甲醇 作用下， 反应 26.0h， 以100%的产率得到di(3-deoxy-3-(4-((butylamino)carbonyl)-1H-1,2,3-triazol-1-yl)-β-D-galactopyranosyl)sulfane
  参考文献：
  名称：

  1H-1,2,3-Triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors

  摘要：

  Galactose C3-triazole derivatives were synthesized by Cu(I)-catalyzed cycloaddition between acetylenes and galactose C3-azido derivatives. Evaluation against galectin-3, 7, 8N (N-terminal) and 9N (N-terminal) revealed 1,4-disubstituted triazoles to be high-affinity inhibitors of galectin-3 with selectivity over galectin-7, 8N, and 9N. Conformational analysis of 1,4-di-and 1,4,5-tri-substituted galactose C3-triazoles suggested that a triazole C5-substituent interfered sterically with the galectin proteins, which explained their poor affinities compared to the corresponding 1,4-disubstituted triazoles. Introduction of two 1,4-disubstituted triazole moieties onto thiodigalactoside resulted in affinities down to 29 nM for galectin-3. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.040

文献信息

• 1H-1,2,3-Triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors
  作者：Bader A. Salameh、Ian Cumpstey、Anders Sundin、Hakon Leffler、Ulf J. Nilsson

  DOI：10.1016/j.bmc.2010.05.040

  日期：2010.7

  Galactose C3-triazole derivatives were synthesized by Cu(I)-catalyzed cycloaddition between acetylenes and galactose C3-azido derivatives. Evaluation against galectin-3, 7, 8N (N-terminal) and 9N (N-terminal) revealed 1,4-disubstituted triazoles to be high-affinity inhibitors of galectin-3 with selectivity over galectin-7, 8N, and 9N. Conformational analysis of 1,4-di-and 1,4,5-tri-substituted galactose C3-triazoles suggested that a triazole C5-substituent interfered sterically with the galectin proteins, which explained their poor affinities compared to the corresponding 1,4-disubstituted triazoles. Introduction of two 1,4-disubstituted triazole moieties onto thiodigalactoside resulted in affinities down to 29 nM for galectin-3. (C) 2010 Elsevier Ltd. All rights reserved.