3α-O-(3'-methylsuccinyl)lithocholic acid | 1292814-23-3

• 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: 3α-O-(3'-methylsuccinyl)lithocholic acid
• 英文别名: 4-[[(3R,5R,8R,9S,10S,13R,14S,17R)-17-[(2R)-4-carboxybutan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-2-methyl-4-oxobutanoic acid
• CAS: 1292814-23-3
• 化学式: C₂₉H₄₆O₆
• 分子量: 490.681
• InChiKey: IFJRUEQOZBUTKY-VNAWNOROSA-N

物化性质

• 熔点：
  164-165 °C
• 沸点：
  625.3±30.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  石胆酸 、 4-(3-Carboxybutanoyloxy)-2-methyl-4-oxobutanoic acid 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 以56%的产率得到3α-O-(3'-methylsuccinyl)lithocholic acid
  参考文献：
  名称：

  Synthesis and proteasome inhibition of lithocholic acid derivatives

  摘要：

  A new class of proteasome inhibitors was synthesized using lithocholic acid as a scaffold. Modification at the C-3 position of lithocholic acid with a series of acid acyl groups yielded compounds with a range of potency on proteasome inhibition. Among them, the phenylene diacetic acid hemiester derivative (13) displayed the most potent proteasome inhibition with IC50 = 1.9 mu M. Enzyme kinetic analysis indicates that these lithocholic acid derivatives are noncompetitive inhibitors of the proteasome. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.041

文献信息

• Synthesis and proteasome inhibition of lithocholic acid derivatives
  作者：Zhao Dang、Andrew Lin、Phong Ho、Dominique Soroka、Kuo-Hsiung Lee、Li Huang、Chin-Ho Chen

  DOI：10.1016/j.bmcl.2011.02.041

  日期：2011.4

  A new class of proteasome inhibitors was synthesized using lithocholic acid as a scaffold. Modification at the C-3 position of lithocholic acid with a series of acid acyl groups yielded compounds with a range of potency on proteasome inhibition. Among them, the phenylene diacetic acid hemiester derivative (13) displayed the most potent proteasome inhibition with IC50 = 1.9 mu M. Enzyme kinetic analysis indicates that these lithocholic acid derivatives are noncompetitive inhibitors of the proteasome. (C) 2011 Elsevier Ltd. All rights reserved.