(3a,5b,6a,12a)-3,6,12-三羟基-胆烷-24-酸 | 21066-18-2

• 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
• 中文名称: (3a,5b,6a,12a)-3,6,12-三羟基-胆烷-24-酸
• 英文名称: 3α,6α,12α-trihydroxy-5β-cholan-24-oic acid
• 英文别名: HDCA；DCA-6α-ol；3alpha,6alpha,12alpha-Trihydroxy-5beta-cholan-24-oic Acid；(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]pentanoic acid
• CAS: 21066-18-2
• 化学式: C₂₄H₄₀O₅
• 分子量: 408.579
• InChiKey: GCAHOAMXTYBLNZ-XUPDPMAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3a,5b,6a,12a)-3,6,12-三羟基-胆烷-24-酸 在 potassium chromate 、 溶剂黄146 作用下， 生成 3α,6α-diacetoxy-12-oxo-5β-cholan-24-oic acid methyl ester
  参考文献：
  名称：

  Takeda; Igarashi, Journal of Biochemistry, 1959, vol. 46, p. 1313,1317

  摘要：

  DOI：
• 作为产物：
  描述：

  胆酸甲酯 在 吡啶 、 2,6-二甲基吡啶 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 samarium diiodide 、 lithium hydroxide monohydrate 、 三氟化硼乙醚 、 水 、 borane tert-butylamine 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 (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

文献信息

• Oral pharmaceutical compositions with sustained release
  申请人：Gipharmex S.p.A.

  公开号：EP0273469A1

  公开（公告）日：1988-07-06

  The present invention relates to a group of compounds of steroidal structure, favourably interfering in alterations of metabolism of cholesterol, and prepared in the form of pharmaceutical compositions with controlled and time-delayed release, suitable for being used with extremely simplified administration plans and with considerable advantages at the level of therapeutical activity.

  本发明涉及一组类固醇结构的化合物，这些化合物能有效地干扰胆固醇代谢的改变，并以药物组合物的形式制备，具有可控和延时释放的特点，适用于极其简化的给药计划，在治疗活性方面具有相当大的优势。
• 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.
• IIDA, TAKASHI;TAMARU, TAMAAKI;CHANG, FREDERIC C.;GOTO, JUNICHI;NAMBARA, T+, J. LIPID RES., 32,(1991) N, C. 649-658
  作者：IIDA, TAKASHI、TAMARU, TAMAAKI、CHANG, FREDERIC C.、GOTO, JUNICHI、NAMBARA, T+

  DOI：——

  日期：——
• SYNTHETIC DERIVATIVES OF CHOLIC ACID 7-SULFATE AND USES THEREOF
  申请人：President and Fellows of Flarvard College

  公开号：US20220016138A1

  公开（公告）日：2022-01-20

  The compositions and methods provided herein are related, in part, to the discovery of cholic acid 7-sulfate as a treatment for diabetes. Provided herein is a method for treating a metabolic disorder (e.g., diabetes, obesity), or an inflammatory disease (e.g., Crohn's disease, inflammatory bowel disease, ulcerative colitis, pancreatitis, hepatitis, appendicitis, gastritis, diverticulitis, celiac disease, food intolerance, enteritis, ulcer, gastroesophageal reflux disease (GERD), psoriatic arthritis, psoriasis, and rheumatoid arthritis) in a subject in need thereof comprising administering to a subject a compound of Formulae (I)-(XVII).
• Takeda; Igarashi, Journal of Biochemistry, 1959, vol. 46, p. 1313,1317
  作者：Takeda、Igarashi

  DOI：——

  日期：——