methyl 2,4,6-tri-O-acetyl-3-(1H-[1,2,3]-triazol-1-yl)-3-deoxy-1-thio-β-D-galactopyranoside | 862670-80-2

• 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-(1H-[1,2,3]-triazol-1-yl)-3-deoxy-1-thio-β-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,5-diacetyloxy-6-methylsulfanyl-4-(triazol-1-yl)oxan-2-yl]methyl acetate
• CAS: 862670-80-2
• 化学式: C₁₅H₂₁N₃O₇S
• 分子量: 387.414
• InChiKey: ZGFAIJGDFPPZPO-FQKPHLNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2,4,6-tri-O-acetyl-3-(1H-[1,2,3]-triazol-1-yl)-3-deoxy-1-thio-β-D-galactopyranoside 在 甲胺 作用下， 以 水 为溶剂， 以90%的产率得到methyl 3-deoxy-3-(1H-{1,2,3}-triazol-1-yl)-1-thio-β-D-galactopyranoside
  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 3-azido-3-deoxy-1-thio-β-D-galactoside 、 丙炔酸 以 甲苯 为溶剂， 反应 17.0h， 以81%的产率得到methyl 2,4,6-tri-O-acetyl-3-(1H-[1,2,3]-triazol-1-yl)-3-deoxy-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

文献信息

• NOVEL 3-TRIAZOLYL-GALACTOSIDE INHIBITORS OF GALECTINS
  申请人：Leffler Hakon

  公开号：US20070185041A1

  公开（公告）日：2007-08-09

  The present invention relates to novel compounds, the use of said compounds as a medicament as well as for the manufacture of a medicament for treatment of disorders relating to the binding of galectin to receptors in a mammal. Said galectin is preferably a galectin-3.

  本发明涉及新型化合物，以及将该化合物用作药物以及制造用于治疗哺乳动物中与galectin与受体结合相关的疾病的药物。所述的galectin通常是galectin-3。
• 3-(1,2,3-Triazol-1-yl)-1-thio-galactosides as small, efficient, and hydrolytically stable inhibitors of galectin-3
  作者：Bader A. Salameh、Hakon Leffler、Ulf J. Nilsson

  DOI：10.1016/j.bmcl.2005.05.084

  日期：2005.7

  Copper(I)-catalyzed addition of alkynes to methyl 3 -azido-3-deoxy-1-thio-beta-D-galactopyrano side afforded stable and structurally simple 3-deoxy-3-(1H-1,2,3-triazol-1-yl)-1-thio-galactosides carrying a panel of substituents at the triazole C4 in high yields. The 3-(1H-[1,2,3]-triazol-1-yl)-1-thio-galactoside collection synthesized contained inhibitors of the tumor- and inflammation-related galectin-3 with K-d values as low as 107 mu M, which is as potent as the natural disaccharide inhibitors lactose and N-acetyllactosamine. (c) 2005 Elsevier Ltd. All rights reserved.
• US7700763B2
  申请人：——

  公开号：US7700763B2

  公开（公告）日：2010-04-20