(2S,3R)-1-(3-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)propylamino)-3-hydroxy-1-oxobutan-2-aminium chloride | 1380092-53-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R)-1-(3-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)propylamino)-3-hydroxy-1-oxobutan-2-aminium chloride
• 英文别名: (2S,3R)-2-amino-N-[3-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)propyl]-3-hydroxybutanamide;hydrochloride
• CAS: 1380092-53-4
• 化学式: C₁₃H₁₈N₂O₆*ClH
• 分子量: 334.757
• InChiKey: BEFQORGIVIHBTC-SXNOSCCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.58
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  150
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  tert-butyl (2S,3R)-3-tert-butoxy-1-(3-(2,5-dimethoxy-3,6-dioxocyclohexa-1,4-dienyl)propylamino)-1-oxobutan-2-ylcarbamate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以80%的产率得到(2S,3R)-1-(3-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)propylamino)-3-hydroxy-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