(2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactospyranosyl)-β(1,4)6-O-acetyl-2-deoxy-2-N-phthalimido-3-bromopropyl-β-D-glucopyranoside | 1421638-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactospyranosyl)-β(1,4)6-O-acetyl-2-deoxy-2-N-phthalimido-3-bromopropyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,5-diacetyloxy-6-[(2R,3S,4R,5R,6R)-2-(acetyloxymethyl)-6-(3-bromopropoxy)-5-(1,3-dioxoisoindol-2-yl)-4-hydroxyoxan-3-yl]oxy-4-azidooxan-2-yl]methyl acetate
• CAS: 1421638-30-3
• 化学式: C₃₁H₃₇BrN₄O₁₅
• 分子量: 785.557
• InChiKey: PDFKBZGUXPVSJN-GAVATHKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  51
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  214
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  (2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactospyranosyl)-β(1,4)6-O-acetyl-2-deoxy-2-N-phthalimido-3-bromopropyl-β-D-glucopyranoside 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.67h， 生成 (3-[4-(4-phenoxyphenyl)-1H-1,2,3-triazol-1-yl]-2,4,6-tri-O-acetyl-3-deoxy-β-D-galactospyranosyl)-β(1,4)-6-O-acetyl-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
• 作为产物：
  描述：

  在 2,4,6-三甲基吡啶 、 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.75h， 生成 (2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactospyranosyl)-β(1,4)6-O-acetyl-2-deoxy-2-N-phthalimido-3-bromopropyl-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