methyl (2a)-2-(2-nitroethyl)-3-oxolup-20(29)en-28-oate | 1381855-10-2

• 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 (2a)-2-(2-nitroethyl)-3-oxolup-20(29)en-28-oate
• 英文别名: methyl (1R,3aS,5aR,5bR,7aR,10S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-10-(2-nitroethyl)-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate
• CAS: 1381855-10-2
• 化学式: C₃₃H₅₁NO₅
• 分子量: 541.772
• InChiKey: CSQHSVMMMPJXEP-LIHWZQMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  路路通酸 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 145.0h， 生成 methyl (2a)-2-(2-nitroethyl)-3-oxolup-20(29)en-28-oate
  参考文献：
  名称：

  Alkylidene branched lupane derivatives: Synthesis and antitumor activity

  摘要：

  Several novel alkylidene branched lupane derivatives have been prepared. Many of these compounds showed a significant cytotoxicity. The most active compound, 2-methylene-betulonic acid, showed IC50 values between 0.2 and 0.6 mu M for 15 different human cancer cell lines. Cytotoxicity can be improved by encapsulation in liposomes. These compounds act by triggering apoptotic cell death as shown by DNA-laddering experiments and acridine orange/ethidium bromide staining. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.023

文献信息

• Alkylidene branched lupane derivatives: Synthesis and antitumor activity
  作者：René Csuk、Sebastian Stark、Christoph Nitsche、Alexander Barthel、Bianka Siewert

  DOI：10.1016/j.ejmech.2012.04.023

  日期：2012.7

  Several novel alkylidene branched lupane derivatives have been prepared. Many of these compounds showed a significant cytotoxicity. The most active compound, 2-methylene-betulonic acid, showed IC50 values between 0.2 and 0.6 mu M for 15 different human cancer cell lines. Cytotoxicity can be improved by encapsulation in liposomes. These compounds act by triggering apoptotic cell death as shown by DNA-laddering experiments and acridine orange/ethidium bromide staining. (C) 2012 Elsevier Masson SAS. All rights reserved.