methyl (1R,7S,8S,9R)-7-acetyloxy-9-[(1E,3E)-5-(aziridin-1-yl)-4-methyl-5-oxopenta-1,3-dienyl]-9-methyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-3-ene-4-carboxylate | 1004752-95-7

• 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: methyl (1R,7S,8S,9R)-7-acetyloxy-9-[(1E,3E)-5-(aziridin-1-yl)-4-methyl-5-oxopenta-1,3-dienyl]-9-methyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-3-ene-4-carboxylate
• CAS: 1004752-95-7
• 化学式: C₂₅H₃₁NO₇
• 分子量: 457.524
• InChiKey: BWWQQWJIRFVSPB-SWXRSRRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-aziridine hydrochloride 、 pseudolaric acid B chloride 在 碳酸氢钠 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以0.050 g的产率得到methyl (1R,7S,8S,9R)-7-acetyloxy-9-[(1E,3E)-5-(aziridin-1-yl)-4-methyl-5-oxopenta-1,3-dienyl]-9-methyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-3-ene-4-carboxylate
  参考文献：
  名称：

  Structural Modification of an Angiogenesis Inhibitor Discovered from Traditional Chinese Medicine and a Structure–Activity Relationship Study

  摘要：

  Pseudolaric acid B (PAB), discovered as a promising angiogensis inhibitor, was served as the anticancer drug lead, and a series of its derivatives were synthesized. Among them, some derivatives, such as 13c-13k, exhibited potent inhibition on the HMEC-1 cell proliferation and strong cytotoxic activities against the tested six tumor cell lines. The PAB derivatives 13c-13k also showed significant and specific inhibition on HMEC-1 cell migration in vitro, and only 13d expressed moderate activity against HMEC-1 cell tube formation. The in vitro anticancer tests of the selected natural PAB analogs and the structurally modified PAB derivatives have led to the establishment of a clear structure-activity relationship.

  DOI：

  10.1021/jm070906g