(1S,4S,5R,9S,10S,13S)-5,9,13-trimethyl-16-methylidene-15-oxo-14-oxatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylic acid | 1363692-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,4S,5R,9S,10S,13S)-5,9,13-trimethyl-16-methylidene-15-oxo-14-oxatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylic acid
• CAS: 1363692-83-4
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: BALYITFKBWRHPF-KIOJNPINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,4S,5R,9S,10S,13S)-5,9,13-trimethyl-16-methylidene-15-oxo-14-oxatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylic acid 、 碘甲烷 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (1S,4S,5R,9S,10S,13S)-5,9,13-trimethyl-16-methylidene-15-oxo-14-oxatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of cytotoxic effects of novel α-methylenelactone tetracyclic diterpenoids

  摘要：

  A series of tetracyclic diterpenoids bearing the alpha-methylenelactone group have been synthesized and screened for their in vitro anti-tumor activities against six human cancer cell lines. The results showed that compounds 1c, 2a and 2b exhibited significant cytotoxicity superior to the positive control doxorubicin hydrochloride against MDA-MB-231, K562 and HepG2 cell lines. In particular, compound 2b was identified as the most promising anticancer agent against HepG2 cells with IC50 value of 0.09 mu M. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.051
• 作为产物：
  描述：

  异甜菊醇 在 4-二甲氨基吡啶 、 pyridinium dichromate 、 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 potassium iodide 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 生成 (1S,4S,5R,9S,10S,13S)-5,9,13-trimethyl-16-methylidene-15-oxo-14-oxatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of cytotoxic effects of novel α-methylenelactone tetracyclic diterpenoids

  摘要：

  A series of tetracyclic diterpenoids bearing the alpha-methylenelactone group have been synthesized and screened for their in vitro anti-tumor activities against six human cancer cell lines. The results showed that compounds 1c, 2a and 2b exhibited significant cytotoxicity superior to the positive control doxorubicin hydrochloride against MDA-MB-231, K562 and HepG2 cell lines. In particular, compound 2b was identified as the most promising anticancer agent against HepG2 cells with IC50 value of 0.09 mu M. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.051