methyl 3α,6α,12α-trihydroxy-5β-cholanoate | 134526-11-7

• 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: methyl 3α,6α,12α-trihydroxy-5β-cholanoate
• 英文别名: methyl 3α,6α-dihydroxy-5β-cholan-24-oate；methyl (4R)-4-[(3R,5R,6S,8R,9S,10R,12S,13R,14S,17R)-3,6,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 134526-11-7
• 化学式: C₂₅H₄₂O₅
• 分子量: 422.605
• InChiKey: GQGPFFUZHUBYNF-QFKJCKFESA-N

物化性质

• 沸点：
  541.6±50.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  86.99
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3α,6α,12α-trihydroxy-5β-cholanoate 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以70%的产率得到(3a,5b,6a,12a)-3,6,12-三羟基-胆烷-24-酸
  参考文献：
  名称：

  一种3α，6α（β），12α-三羟基-5β-胆酸的合成方法

  摘要：

  本发明公开了3α，6α，12α‑三羟基‑5β‑胆酸和3α，6β，12α‑三羟基‑5β‑胆酸的合成方法，以3α，7α，12α‑三羟基‑5β‑胆酸为原料，经Mukaiyama羟醛缩合反应、氧化裂解、还原脱除等十步反应制得3α，6α，12α‑三羟基‑5β‑胆酸和3α，6β，12α‑三羟基‑5β‑胆酸。本发明合成方法绿色、高效的特点。

  公开号：

  CN111718389B
• 作为产物：
  描述：

  methyl (4R)-4-[(5R,6S,8R,9S,10R,12S,13R,14S,17R)-6,12-dihydroxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate 以82%的产率得到
  参考文献：
  名称：

  IIDA, TAKASHI;TAMARU, TAMAAKI;CHANG, FREDERIC C.;GOTO, JUNICHI;NAMBARA, T+, J. LIPID RES., 32,(1991) N, C. 649-658

  摘要：

  DOI：

文献信息

• Structural analysis and antitussive evaluation of five novel esters of verticinone and bile acids
  作者：Jiu-liang Zhang、Hui Wang、Hui-fang Pi、Han-li Ruan、Peng Zhang、Ji-zhou Wu

  DOI：10.1016/j.steroids.2008.12.007

  日期：2009.4

  Shedan-Chuanbei powder, a complex of traditional Chinese medicine preparation, which consists of Snake Bile (Chinese name "Shedan") and Fritillariae Cirrhosae (Chinese name "Chuanbei"), is the most popular antitussive and expectorant formulation in Chinese communities. However, the clinical application of Shedan-Chuanbei powder is now stringently limited because of the shortage of the two crude medicinal materials, especially for the sake of animal protection. In addition, the inherent defects of the most of the complex of traditional Chinese medicine such as the indistinct basal phartnacodynamic materials and the difficulties in quality control had blocked them heading into the international medicinal market. So we attempted to seek new substitute for Shedan-Chuanbei powder for antitussive drugs. In order to gain some new compounds with better bioactivity and attenuated toxicity, we tried to combine two kinds of drugs through ester bond. Enlightened with "combination principle" in drug discovery, we synthesized five novel esters of verticinone and bile acids, both of which are the major bioactive components in Shedan-Chuanbei powder. We then evaluated the antitussive activity and the acute toxicity of the five ester-linked compounds. The five ester-linked Compounds had much more potent antitussive activity and expectorant activity than single bile acids at the same doses, and had equivalent antitussive activity and expectorant activity in comparison with about double moles dose of the monomer verticinone. Especially, cholic acid-verticinone ester had much more potent antitussive effects than the monomer verticinone or cholic acid at the same dose. A further acute toxicity study showed that the LD50 values of the five ester-linked compounds exceeded 3.5 g/kg by intraperitoneal injection in mice. Based on the studies of pharmacology and acute toxicity, the five ester-linked compounds have synergic pharmacodynamic action and attenuated toxicity compared with single verticinone and single bile acids. (C) 2008 Elsevier Inc. All rights reserved.