(3R,3aR,5aR,5bS,7aR,10R,11S,11aR,13bS)-2-hydroxy-3-(methoxycarbonyl)-3,5a,5b,7a,10,11,13b-heptamethyl-13-oxo-2,3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-2-carboxylic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3R,3aR,5aR,5bS,7aR,10R,11S,11aR,13bS)-2-hydroxy-3-(methoxycarbonyl)-3,5a,5b,7a,10,11,13b-heptamethyl-13-oxo-2,3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-2-carboxylic acid
• 英文别名: (3R,3aR,5aR,5bS,7aR,10R,11S,11aR,13aR,13bS)-2-hydroxy-3-methoxycarbonyl-3,5a,5b,7a,10,11,13b-heptamethyl-13-oxo-1,3a,4,5,6,7,8,9,10,11,11a,13a-dodecahydrocyclopenta[a]chrysene-2-carboxylic acid
• 化学式: C₃₁H₄₆O₆
• 分子量: 514.703
• InChiKey: SOLVHHLTBPJEFY-TZQRXUNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰基-11-酮基-beta-乳香酸 在 草酰氯 、 溴 、 potassium carbonate 、 caesium carbonate 、 溶剂黄146 、 二甲基亚砜 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 51.25h， 生成 (3R,3aR,5aR,5bS,7aR,10R,11S,11aR,13bS)-2-hydroxy-3-(methoxycarbonyl)-3,5a,5b,7a,10,11,13b-heptamethyl-13-oxo-2,3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and antitumor activity of ring A modified 11-keto-β-boswellic acid derivatives

  摘要：

  Beta-boswellic acids are interesting triterpenoic acids that show different biological activities. Their cytotoxic potential, as well as that of their derivates remained unexploited so far. In this study we were able to prepare derivatives of 11-keto-beta-boswellic acid that showed lower IC50 values as determined by a sulphorhodamine B (SRB) assay using several different human tumour cell lines. Thus, the introduction of an amino group at position C-2 led to a significantly improved cytotoxic activity of amine 18. An apoptotic effect of compound 18 was determined using DNA laddering and trypan blue staining experiments. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.039

文献信息

• Synthesis and antitumor activity of ring A modified 11-keto-β-boswellic acid derivatives
  作者：René Csuk、Anja Niesen-Barthel、Renate Schäfer、Alexander Barthel、Ahmed Al-Harrasi

  DOI：10.1016/j.ejmech.2015.01.039

  日期：2015.3

  Beta-boswellic acids are interesting triterpenoic acids that show different biological activities. Their cytotoxic potential, as well as that of their derivates remained unexploited so far. In this study we were able to prepare derivatives of 11-keto-beta-boswellic acid that showed lower IC50 values as determined by a sulphorhodamine B (SRB) assay using several different human tumour cell lines. Thus, the introduction of an amino group at position C-2 led to a significantly improved cytotoxic activity of amine 18. An apoptotic effect of compound 18 was determined using DNA laddering and trypan blue staining experiments. (C) 2015 Elsevier Masson SAS. All rights reserved.