(2E,4E)-5-[(1R,7S,8S,9R)-4-methoxycarbonyl-9-methyl-11-oxo-7-propanoyloxy-10-oxatricyclo[6.3.2.01,7]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid | 1004752-96-8

• 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: (2E,4E)-5-[(1R,7S,8S,9R)-4-methoxycarbonyl-9-methyl-11-oxo-7-propanoyloxy-10-oxatricyclo[6.3.2.01,7]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid
• CAS: 1004752-96-8
• 化学式: C₂₄H₃₀O₈
• 分子量: 446.497
• InChiKey: USXZUUGIHLNJMW-QNSGMBKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  丙酰氯 、 土槿皮乙酸 在 potassium tert-butylate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 48.0h， 生成 (2E,4E)-5-[(1R,7S,8S,9R)-4-methoxycarbonyl-9-methyl-11-oxo-7-propanoyloxy-10-oxatricyclo[6.3.2.01,7]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid
  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

文献信息

• Structural Modification of an Angiogenesis Inhibitor Discovered from Traditional Chinese Medicine and a Structure–Activity Relationship Study
  作者：Sheng-Ping Yang、Yu-Jun Cai、Bang-Le Zhang、Lin-Jiang Tong、Hua Xie、Yan Wu、Li-Ping Lin、Jian Ding、Jian-Min Yue

  DOI：10.1021/jm070906g

  日期：2008.1.1

  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.