(3-[4-(4-phenoxyphenyl)-1H-1,2,3-triazol-1-yl]-3-deoxy-β-D-galactospyranosyl)-β(1,4)-2-deoxy-2-N-phthalimido-3-azidopropyl-β-D-glucopyranoside | 1421638-33-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-[4-(4-phenoxyphenyl)-1H-1,2,3-triazol-1-yl]-3-deoxy-β-D-galactospyranosyl)-β(1,4)-2-deoxy-2-N-phthalimido-3-azidopropyl-β-D-glucopyranoside
• 英文别名: 2-[(2R,3R,4R,5S,6R)-2-(3-azidopropoxy)-5-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[4-(4-phenoxyphenyl)triazol-1-yl]oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 1421638-33-6
• 化学式: C₃₇H₃₉N₇O₁₂
• 分子量: 773.756
• InChiKey: CMRMTZCSSSYBBI-ZGYIDIDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  56
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  230
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (3-[4-(4-phenoxyphenyl)-1H-1,2,3-triazol-1-yl]-3-deoxy-β-D-galactospyranosyl)-β(1,4)-2-deoxy-2-N-phthalimido-3-azidopropyl-β-D-glucopyranoside 在 乙二胺 、 N,N-二异丙基乙胺 作用下， 以 乙腈 、 正丁醇 为溶剂， 反应 21.0h， 生成 (3-[4-(4-phenoxyphenyl)-1H-1,2,3-triazol-1-yl]-3-deoxy-β-D-galactospyranosyl)-β(1,4)-2-deoxy-2-N-benzamido-3-azidopropyl-β-D-glucopyranoside
  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：

  4-苯氧基苯乙炔 在 甲醇 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium methylate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 生成 (3-[4-(4-phenoxyphenyl)-1H-1,2,3-triazol-1-yl]-3-deoxy-β-D-galactospyranosyl)-β(1,4)-2-deoxy-2-N-phthalimido-3-azidopropyl-β-D-glucopyranoside
  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

文献信息

• Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1
  作者：Hilde van Hattum、Hilbert M. Branderhorst、Ed E. Moret、Ulf J. Nilsson、Hakon Leffler、Roland J. Pieters

  DOI：10.1021/jm301677r

  日期：2013.2.14

  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.