methyl 2,4,6-tri-O-acetyl-3-deoxy-3-(4-(2-fluorophenyl)-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside | 1242965-11-2

• 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-(2-fluorophenyl)-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside
• CAS: 1242965-11-2
• 化学式: C₂₁H₂₄FN₃O₇S
• 分子量: 481.502
• InChiKey: QYQZOPUVURHRTJ-IFLJBQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  118.84
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 2,4,6-tri-O-acetyl-3-deoxy-3-(4-(2-fluorophenyl)-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside 在 水 、 甲胺 作用下， 以82%的产率得到methyl 3-deoxy-3-{4-(2-fluorophenyl)-1H-[1,2,3]-triazol-1-yl}-1-thio-β-D-galactopyranoside
  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
• 作为产物：
  描述：

  methyl 3-azido-3-deoxy-1-thio-β-D-galactoside 、 1-乙炔基-2-氟苯 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以99%的产率得到methyl 2,4,6-tri-O-acetyl-3-deoxy-3-(4-(2-fluorophenyl)-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside
  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