24-去甲-5beta-胆烷-23-酸 | 511-18-2

• 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: 24-去甲-5beta-胆烷-23-酸
• 英文名称: 24-nor-5β-cholanoic acid
• 英文别名: 24-nor-5β-cholanoic acid-(23)；24-Nor-5β-cholansaeure-(23)；norcholanic acid；(3R)-3-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]butanoic acid
• CAS: 511-18-2
• 化学式: C₂₃H₃₈O₂
• 分子量: 346.554
• InChiKey: UNDDRXNWYMVMIX-RDIILWCNSA-N

物化性质

• 熔点：
  177°
• 沸点：
  421.26°C (rough estimate)
• 密度：
  1.0136 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  24-去甲-5beta-胆烷-23-酸 在 chromium(VI) oxide 、 盐酸 、 乙醚 、 溶剂黄146 作用下， 生成 23-phenyl-24-nor-5β-cholanone-(23)
  参考文献：
  名称：

  Wieland; Schlichting; Jacobi, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1926, vol. 161, p. 80,102

  摘要：

  DOI：
• 作为产物：
  描述：

  3α-formyloxy-5β-cholan-24-oic acid 在 吡啶 、 palladium hydroxide, 20 wt% on carbon 、 氢气 、 lithium carbonate 、 对甲苯磺酸 、 三氟乙酸 、 三氟乙酸酐 、 potassium hydroxide 、 lithium bromide 、 sodium hydroxide 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 24-去甲-5beta-胆烷-23-酸
  参考文献：
  名称：

  Investigation on bile acid receptor regulators. Discovery of cholanoic acid derivatives with dual G-protein coupled bile acid receptor 1 (GPBAR1) antagonistic and farnesoid X receptor (FXR) modulatory activity

  摘要：

  Bile acids, the end products of cholesterol metabolism, activate multiple mechanisms through the interaction with membrane G-protein coupled receptors including the bile acid receptor GPBAR1 and nuclear receptors such as the bile acid sensor, farnesoid X receptor (FXR). Even if dual FXR/GPBAR1 agonists are largely considered a novel opportunity in the treatment of several liver and metabolic diseases, selective targeting of one of these receptors represents an attractive therapeutic approach for a wide range of disorders in which dual modulation is associated to severe side effects. In the present study we have investigated around the structure of LCA generating a small library of cholane derivatives, endowed with dual FXR agonism/GPBAR1 antagonism. To the best of our knowledge, this is the first report of bile acid derivatives able to antagonize GPBAR1. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.11.003

文献信息

• [EN] OPTIMIZED SYNTHESIS OF PURE, NON-POLYMORPHIC, CRYSTALLINE BILE ACIDS WITH DEFINED PARTICLE SIZE<br/>[FR] SYNTHÈSE OPTIMISÉE D'ACIDES BILIAIRES CRISTALLINS PURS ET NON POLYMORPHES AYANT UNE TAILLE DÉFINIE DE PARTICULE
  申请人：FALK PHARMA GMBH

  公开号：WO2012072689A1

  公开（公告）日：2012-06-07

  The present invention relates to a pure polymorph of Nor-UDCA or Bis-nor-UDCA, or of a pharmaceutically acceptable salt thereof. The invention further provides a pharmaceutical composition comprising the polymorph of the invention, and a method for preparing the polymorph. The invention includes the pharmaceutical use of the polymorph or of the pharmaceutical composition of the invention.

  本发明涉及Nor-UDCA或Bis-nor-UDCA的纯多型，或其药用盐。本发明还提供了包括该多型的药物组合物，以及制备该多型的方法。本发明包括使用该多型或本发明的药物组合物的药用。
• Bile-acid derived compounds for providing sustained systemic concentrations of drugs after oral administration
  申请人：Cundy C. Kenneth

  公开号：US20050272710A1

  公开（公告）日：2005-12-08

  This invention is directed to methods for providing sustained systemic concentrations of therapeutic or prophylactic agents such as GABA analogs following oral administration to animals. This invention is also directed to compounds and pharmaceutical compositions that are used in such methods.

  本发明涉及提供治疗或预防剂量如GABA类似物的持续系统浓度的方法，该方法通过口服给动物。本发明还涉及用于这种方法的化合物和药物组合物。
• Optimized synthesis of pure, non-polymorphic, crystalline bile acids with defined particle size
  申请人：Dr. Falk Pharma GmbH

  公开号：US10000526B2

  公开（公告）日：2018-06-19

  The present invention relates to a pure polymorph of Nor-UDCA or Bis-nor-UDCA, or of a pharmaceutically acceptable salt thereof. The invention further provides a pharmaceutical composition comprising the polymorph of the invention, and a method for preparing the polymorph. The invention includes the pharmaceutical use of the polymorph or of the pharmaceutical composition of the invention.

  本发明涉及一种纯净的 Nor-UDCA 或 Bis-nor-UDCA 多晶体，或其药学上可接受的盐。本发明进一步提供了一种包含本发明多晶型的药物组合物，以及制备该多晶型的方法。本发明包括本发明多晶型或本发明药物组合物的药物用途。
• Wieland; Jacobi, Chemische Berichte, 1926, vol. 59, p. 2064,2065
  作者：Wieland、Jacobi

  DOI：——

  日期：——
• 98. The synthesis of 5 : 6-dimethyl-1 : 2-benzanthraquinone, a degradation product of deoxycholic acid
  作者：J. W. Cook、G. A. D. Haslewood

  DOI：10.1039/jr9340000428

  日期：——