(2S,3R)-3-(benzyloxy)-1-((2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)methylamino)-1-oxobutan-2-aminium chloride | 1380092-47-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-3-(benzyloxy)-1-((2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)methylamino)-1-oxobutan-2-aminium chloride
• 英文别名: (2S,3R)-2-amino-N-[(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-3-phenylmethoxybutanamide;hydrochloride
• CAS: 1380092-47-6
• 化学式: C₁₈H₂₀N₂O₆*ClH
• 分子量: 396.828
• InChiKey: XTZHTUUKGUPZOG-VSLILLSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  139
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  tert-butyl (2S,3R)-3-(benzyloxy)-1-((2,5-dimethoxy-3,6-dioxocyclohexa-1,4-dienyl)methylamino)-1-oxobutan-2-ylcarbamate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以79%的产率得到(2S,3R)-3-(benzyloxy)-1-((2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)methylamino)-1-oxobutan-2-aminium chloride
  参考文献：
  名称：

  Synthesis and biological evaluation of hydrophilic embelin derivatives

  摘要：

  In continuance of our search for newer anti-cancer agents we were interested on embelin, a XIAP (X-linked inhibitor of apoptosis protein) inhibitor. This natural benzoquinone bear a lipophilic chain and we report here the synthesis of hydrophilic analogues of embelin. To allow a large flexibility in the nature of the hydrophilic group, three amines with different length of carbon chain bearing a protected benzoquinone were prepared. The cytotoxic effects of these derivatives were evaluated on KB cell line. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.024