methyl 2,4,6-tri-O-acetyl-3-deoxy-3-(4-(1-hydroxycyclohexyl)-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside | 862670-79-9

• 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-(1-hydroxycyclohexyl)-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside
• 英文别名: methyl 2,4,6-tri-O-acetyl-3-deoxy-3-(4-(1-hydroxy-1-cyclohexyl)-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside；[(2R,3R,4S,5R,6S)-3,5-diacetyloxy-4-[4-(1-hydroxycyclohexyl)triazol-1-yl]-6-methylsulfanyloxan-2-yl]methyl acetate
• CAS: 862670-79-9
• 化学式: C₂₁H₃₁N₃O₈S
• 分子量: 485.558
• InChiKey: FGZLFPDBWPARLP-ZKIDJSGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2,4,6-tri-O-acetyl-3-deoxy-3-(4-(1-hydroxycyclohexyl)-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside 在 甲胺 作用下， 以87%的产率得到methyl 3-deoxy-3-(4-(1-hydroxy-1-cyclohexyl)-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  3-(1,2,3-Triazol-1-yl)-1-thio-galactosides as small, efficient, and hydrolytically stable inhibitors of galectin-3

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2005.05.084
• 作为产物：
  描述：

  methyl 3-azido-3-deoxy-1-thio-β-D-galactoside 、 炔环己醇 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96%的产率得到methyl 2,4,6-tri-O-acetyl-3-deoxy-3-(4-(1-hydroxycyclohexyl)-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