methyl 3-(4-benzylaminocarbonyl-1H-[1,2,3]-triazol-1-yl)-3-deoxy-β-D-galactopyranosyl-(14)-2-acetamido-2-deoxy-β-D-glucopyranoside | 1242965-33-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-(4-benzylaminocarbonyl-1H-[1,2,3]-triazol-1-yl)-3-deoxy-β-D-galactopyranosyl-(14)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: 1-[(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]-N-benzyltriazole-4-carboxamide
• CAS: 1242965-33-8
• 化学式: C₂₅H₃₅N₅O₁₁
• 分子量: 581.58
• InChiKey: WSKGVZYQSPPRJM-ADXYMSLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  227
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  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 、 苄胺 在 甲醇 作用下， 反应 72.0h， 以81%的产率得到methyl 3-(4-benzylaminocarbonyl-1H-[1,2,3]-triazol-1-yl)-3-deoxy-β-D-galactopyranosyl-(14)-2-acetamido-2-deoxy-β-D-glucopyranoside
  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.