15-oxo-16-exo-methylenebeyerane-19-acid | 1266676-05-4

• 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: 15-oxo-16-exo-methylenebeyerane-19-acid
• 英文别名: (1S,4S,5R,9S,10S,13S)-5,9,13-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 1266676-05-4
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: VOOUXHQGPJYYDO-XNRDYXSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  15-hydroxy-16-exo-methylenebeyerane-19-acid 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以70.5%的产率得到15-oxo-16-exo-methylenebeyerane-19-acid
  参考文献：
  名称：

  Synthesis and biological evaluation of novel exo-methylene cyclopentanone tetracyclic diterpenoids as antitumor agents

  摘要：

  The structure of exo-methylene cyclopentanone, which exists in nature tetracyclic diterpenoids products, has been proved to be an innate group for the treatment of cancer and inflammation. In this letter, four different scaffolds of tetracyclic diterpenoids including the structure exo-methylene cyclopentanone were synthesized from steviol and isosteviol and evaluated in vitro for their antitumor activity against three human cancer lines. Compounds 1a, 1b, 2b and 3b showed significant cytotoxicity, particularly, tetracyclic diterpenoids 2b, 3b were identified as the most potent and selective anticancer agents superior to adriamycin with IC50 values of 0.9 mu M and 1.5 mu M, against Hep-G2 and MDA-MB-231 cell lines, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.055

文献信息

• Synthesis and biological evaluation of novel exo-methylene cyclopentanone tetracyclic diterpenoids as antitumor agents
  作者：Jing Li、Dayong Zhang、Xiaoming Wu

  DOI：10.1016/j.bmcl.2010.11.055

  日期：2011.1

  The structure of exo-methylene cyclopentanone, which exists in nature tetracyclic diterpenoids products, has been proved to be an innate group for the treatment of cancer and inflammation. In this letter, four different scaffolds of tetracyclic diterpenoids including the structure exo-methylene cyclopentanone were synthesized from steviol and isosteviol and evaluated in vitro for their antitumor activity against three human cancer lines. Compounds 1a, 1b, 2b and 3b showed significant cytotoxicity, particularly, tetracyclic diterpenoids 2b, 3b were identified as the most potent and selective anticancer agents superior to adriamycin with IC50 values of 0.9 mu M and 1.5 mu M, against Hep-G2 and MDA-MB-231 cell lines, respectively. (C) 2010 Elsevier Ltd. All rights reserved.