(3-O-(4-phenoxybenzyl)-β-D-galactopyranosyl)-β-(1,4)-2-deoxy-2-N-phthalimido-3-azidopropyl-β-D-glucopyranoside | 1421638-28-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-O-(4-phenoxybenzyl)-β-D-galactopyranosyl)-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,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(4-phenoxyphenyl)methoxy]oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 1421638-28-9
• 化学式: C₃₆H₄₀N₄O₁₃
• 分子量: 736.733
• InChiKey: WMKQBCBZKSFTKY-IUKAKSITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  208
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (3-O-(4-phenoxybenzyl)-β-D-galactopyranosyl)-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-O-(4-phenoxybenzyl)-β-D-galactopyranosyl)-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：

  2-脱氧-2-苯二酰亚胺-1,3,4,6-四-氧-乙酰-β-D-吡喃葡萄糖 在 2,4,6-三甲基吡啶 、 甲醇 、 N-碘代丁二酰亚胺 、 sodium azide 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 32.75h， 生成 (3-O-(4-phenoxybenzyl)-β-D-galactopyranosyl)-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.