methyl 3-deoxy-3-(4,5-bis(methylaminocarbonyl)-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside | 1242965-26-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 3-deoxy-3-(4,5-bis(methylaminocarbonyl)-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside
• 英文别名: 1-[(2R,3R,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-methylsulfanyloxan-4-yl]-4-N,5-N-dimethyltriazole-4,5-dicarboxamide
• CAS: 1242965-26-9
• 化学式: C₁₃H₂₁N₅O₆S
• 分子量: 375.406
• InChiKey: SXWFWOJAMMBXOC-JBCZCILTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  184
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl 2,4,6-tri-O-acetyl-3-(4,5-bis-methoxycarbonyl-1H-[1,2,3]-triazol-1-yl)-3-deoxy-1-thio-β-D-galactopyranoside 、 甲胺 在 水 作用下， 反应 12.0h， 以92%的产率得到methyl 3-deoxy-3-(4,5-bis(methylaminocarbonyl)-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