methyl 2,4,6-tri-O-acetyl-3-deoxy-3-(4-methoxycarbonyl-1H-[1,2,3]-triazol-1-yl)-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside | 869957-47-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4,6-tri-O-acetyl-3-deoxy-3-(4-methoxycarbonyl-1H-[1,2,3]-triazol-1-yl)-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: methyl 2,4,6-tri-O-acetyl-3-deoxy-3-(4-methoxycarbonyl-1H-[1,2,3]-triazol-1-yl)-β-D-galactopyranosyl-(1-4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside；methyl 1-[(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-5-acetamido-4-acetyloxy-2-(acetyloxymethyl)-6-methoxyoxan-3-yl]oxy-3,5-diacetyloxy-6-(acetyloxymethyl)oxan-4-yl]triazole-4-carboxylate
• CAS: 869957-47-1
• 化学式: C₂₉H₄₀N₄O₁₇
• 分子量: 716.653
• InChiKey: UOBRNPMRDDOQIM-YHOIDUCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  255
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  methyl 2,4,6-tri-O-acetyl-3-deoxy-3-(4-methoxycarbonyl-1H-[1,2,3]-triazol-1-yl)-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside 、 甲胺 以 水 为溶剂， 反应 12.0h， 以80%的产率得到methyl 3-(4-methylaminocarbonyl-1H-[1,2,3]-triazol-1-yl)-3-deoxy-β-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  [EN] NOVEL 3-TRIAZOLYL-GALACTOSIDE INHIBITORS OF GALECTINS
  [FR] NOUVEAUX INHIBITEURS DE GALECTINES CONTENANT 3-TRIAZOLYL-GALACTOSIDE

  摘要：

  本发明涉及新型3-三唑基半乳糖苷，以及将该三唑基半乳糖苷用作药物以及制造用于治疗哺乳动物中与半乳糖结合到受体相关的疾病的药物。所述的半乳糖最好是半乳糖-3。

  公开号：

  WO2005113569A1
• 作为产物：
  描述：

  methyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl-(1-4)-2-acetamido-6-O-acetyl-2-deoxy-β-D-glucopyranoside 在 copper(l) iodide N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 methyl 2,4,6-tri-O-acetyl-3-deoxy-3-(4-methoxycarbonyl-1H-[1,2,3]-triazol-1-yl)-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  [EN] NOVEL 3-TRIAZOLYL-GALACTOSIDE INHIBITORS OF GALECTINS
  [FR] NOUVEAUX INHIBITEURS DE GALECTINES CONTENANT 3-TRIAZOLYL-GALACTOSIDE

  摘要：

  本发明涉及新型3-三唑基半乳糖苷，以及将该三唑基半乳糖苷用作药物以及制造用于治疗哺乳动物中与半乳糖结合到受体相关的疾病的药物。所述的半乳糖最好是半乳糖-3。

  公开号：

  WO2005113569A1

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.