(R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-((3-carboxypropanoyl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid | 87826-99-1

• 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: (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-((3-carboxypropanoyl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
• 英文别名: 3α-O-succinyllithocholic acid；3alpha-(3-Carboxypropanoyloxy)-5beta-cholanic acid；(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-(3-carboxypropanoyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 87826-99-1
• 化学式: C₂₈H₄₄O₆
• 分子量: 476.654
• InChiKey: DFOFHELKYLKULT-XBBAIHCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-((3-carboxypropanoyl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid 在 4-二甲氨基吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 苯 为溶剂， 反应 12.0h， 生成 Succinic acid 8-bromo-octyl ester (3R,5R,8R,9S,10S,13R,14S,17R)-17-[(R)-3-(8-bromo-octyloxycarbonyl)-1-methyl-propyl]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Effect of a Lithocholic Acid Derivative on the Molecular Packing and Stability of Phospholipid Vesicles

  摘要：

  合成了一种与磷脂具有高兼容性的石胆酸衍生物，并将其嵌入磷脂双分子膜中。通过荧光去极化方法和浊度测量，分别阐明了它对分子堆积和囊泡悬浮液稳定性增强的显著影响。

  DOI：

  10.1246/cl.1994.2199
• 作为产物：
  描述：

  丁二酸酐 、 石胆酸 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 15.0h， 以60%的产率得到(R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-((3-carboxypropanoyl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
  参考文献：
  名称：

  Lithocholic acid analogues, new and potent α-2,3-sialyltransferase inhibitors

  摘要：

  一种新型非竞争性α-2,3-唾液酸转移酶抑制剂已被合成；我们报告了十六种石胆酸类似物的发现、制备及其抑制活性。

  DOI：

  10.1039/b514915k

文献信息

• Synthesis of Novel Steroid-Peptoid Hybrid Macrocycles by Multiple Multicomponent Macrocyclizations Including Bifunctional Building Blocks (MiBs)
  作者：Daniel Rivera、Ludger Wessjohann

  DOI：10.3390/12081890

  日期：——

  pseudo-amino acid by an Ugi-4CR-based cyclooligomerization approach. Both types of macrocycles are steroid-peptoid hybrid macrocycles containing exocyclic peptidic chains. These novel frameworks are a result of the use of bile acids bifunctionalized with carboxylic and amino functionalities as bifunctional building blocks of the Ugi-MiB approach.

  通过实施 MiB 方法的新颖组合，产生了两组新的胆烷-类肽杂化大环化合物。通过在基于双向双 Ugi-四组分 (Ugi-4CR) 的大环化方案中利用胆烷二羧酸和二胺，获得了包含杂环和芳基部分的基于类固醇的杂化大环内酰胺。或者，通过基于 Ugi-4CR 的环寡聚方法从胆烷假氨基酸生产 N-取代的环胆酰胺。两种类型的大环化合物都是含有环外肽链的类固醇-类肽杂化大环化合物。这些新颖的框架是使用羧基和氨基双功能化的胆汁酸作为 Ugi-MiB 方法的双功能构建块的结果。
• 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.
• Lithocholic acid analogues, new and potent α-2,3-sialyltransferase inhibitors
  作者：Kai-Hsuan Chang、Lenselot Lee、Jessica Chen、Wen-Shan Li

  DOI：10.1039/b514915k

  日期：——

  A new type of noncompetitive α-2,3-sialyltransferase inhibitor has been synthesized; we report the discovery, preparation and inhibitory activity of sixteen lithocholic acid analogues.

  一种新型非竞争性α-2,3-唾液酸转移酶抑制剂已被合成；我们报告了十六种石胆酸类似物的发现、制备及其抑制活性。
• Effect of a Lithocholic Acid Derivative on the Molecular Packing and Stability of Phospholipid Vesicles
  作者：Zi-Chen Li、Fu-Mian Li、Shinya Arase、Shinji Takeoka、Eishun Tsuchida

  DOI：10.1246/cl.1994.2199

  日期：1994.12

  A lithocholic acid derivative having high compatibility with phospholipid was synthesized and incorporated to the phospholipid bilayer membrane. A significant influence of it on the molecular packing and the stability enhancement of the vesicle suspension were clarified by a fluorescence depolarization method and a turbidity measurement, respectively.

  合成了一种与磷脂具有高兼容性的石胆酸衍生物，并将其嵌入磷脂双分子膜中。通过荧光去极化方法和浊度测量，分别阐明了它对分子堆积和囊泡悬浮液稳定性增强的显著影响。