[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl] 3-[4-[(7-chloroquinolin-4-yl)amino]butylamino]propanoate | 1309957-07-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl] 3-[4-[(7-chloroquinolin-4-yl)amino]butylamino]propanoate
• CAS: 1309957-07-0
• 化学式: C₃₁H₄₂ClN₃O₆
• 分子量: 588.144
• InChiKey: PUSFAASILSUVRH-HMLYFKECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  dihydroartemisinin 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 [(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl] 3-[4-[(7-chloroquinolin-4-yl)amino]butylamino]propanoate
  参考文献：
  名称：

  Antiplasmodial and antitumor activity of dihydroartemisinin analogs derived via the aza-Michael addition reaction

  摘要：

  A series of dihydroartemisinin derivatives were synthesized via an aza-Michael addition reaction to a dihydroartemisinin-based acrylate and were evaluated for antiplasmodial and antitumor activity. The target compounds showed excellent antiplasmodial activity, with dihydroartemisinin derivatives 5, 7, 9 and 13 exhibiting IC50 values of <= 10 nM against both D10 and Dd2 strains of Plasmodium falciparum. Derivative 4d was the most active against the HeLa cancer cell line, with an IC50 of 0.37 mu M and the highest tumor specificity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.090