bis-{2,4,6-tri-O-acetyl-3-deoxy-3-[4-(3-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]-β-D-galactopyranosyl}sulfane | 1421638-22-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis-{2,4,6-tri-O-acetyl-3-deoxy-3-[4-(3-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]-β-D-galactopyranosyl}sulfane
• 英文别名: [(2R,3R,4S,5R,6S)-3,5-diacetyloxy-6-[(2S,3R,4S,5R,6R)-3,5-diacetyloxy-6-(acetyloxymethyl)-4-[4-(3-hydroxyphenyl)triazol-1-yl]oxan-2-yl]sulfanyl-4-[4-(3-hydroxyphenyl)triazol-1-yl]oxan-2-yl]methyl acetate
• CAS: 1421638-22-3
• 化学式: C₄₀H₄₄N₆O₁₆S
• 分子量: 896.886
• InChiKey: QPNQYAWVAGWBKK-YXBMSDDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  63
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  303
• 氢给体数：
  2
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  bis-{2,4,6-tri-O-acetyl-3-deoxy-3-[4-(3-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]-β-D-galactopyranosyl}sulfane 在 甲醇 、 sodium methylate 作用下， 反应 2.5h， 以86%的产率得到bis-{3-deoxy-3-[4-(3-hydoxyphenyl)-1H-1,2,3-triazol-1-yl]-β-D-galactopyranosyl}sulfane
  参考文献：
  名称：

  Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1

  摘要：

  Inhibitors for galectin-1 and -3 were synthesized from thiodigalactoside and lactosamine by derivatization of the galactose C3. Introduction of 4-phenyl-1H-1,2,3-triazol-1-yl substituents at the thiodigalactoside C3 by CuAAC, targeting arginine-arene interactions, increased the affinity to 13 nM but yielded little selectivity. The builder 4-(4-phenoxypheny1)-1H-1,2,3-triazol-1-yl substituent, however, increased the preference for galectin-3 over galectin-1 to more than 200-fold. Modeling showed more arginine-arene interactions for galectin-3 than for galectin-1. Introducing 4-phenoxyaryl groups on lactosamine had a similar effect.

  DOI：

  10.1021/jm301677r
• 作为产物：
  描述：

  bis(2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl)sulfane 、 3-羟基苯基乙炔 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以100%的产率得到bis-{2,4,6-tri-O-acetyl-3-deoxy-3-[4-(3-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]-β-D-galactopyranosyl}sulfane
  参考文献：
  名称：

  Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1

  摘要：

  Inhibitors for galectin-1 and -3 were synthesized from thiodigalactoside and lactosamine by derivatization of the galactose C3. Introduction of 4-phenyl-1H-1,2,3-triazol-1-yl substituents at the thiodigalactoside C3 by CuAAC, targeting arginine-arene interactions, increased the affinity to 13 nM but yielded little selectivity. The builder 4-(4-phenoxypheny1)-1H-1,2,3-triazol-1-yl substituent, however, increased the preference for galectin-3 over galectin-1 to more than 200-fold. Modeling showed more arginine-arene interactions for galectin-3 than for galectin-1. Introducing 4-phenoxyaryl groups on lactosamine had a similar effect.

  DOI：

  10.1021/jm301677r