3α,7α,16β-trihydroxy-6α-ethyl-5β-cholan-24-oic acid sodium salt | 1227612-58-9

• 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,7α,16β-trihydroxy-6α-ethyl-5β-cholan-24-oic acid sodium salt
• 英文别名: 6α-ethyl-16-epi-avicholic acid sodium salt；sodium;(4R)-4-[(3R,5S,6R,7R,8R,9S,10S,13S,14S,16S,17R)-6-ethyl-3,7,16-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: 1227612-58-9
• 化学式: C₂₆H₄₃O₅*Na
• 分子量: 458.614
• InChiKey: FJWJKQXCFIAJTO-DNTMIVBCSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.25
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  奥贝胆酸杂质48 在 吡啶 、 甲醇 、 Jones reagent 、 calcium hydride 、 硼烷四氢呋喃络合物 、 (二氯碘)-苯 、 硼烷-叔丁基胺 、 苄基三乙基氯化铵 、 碳酸氢钠 、 对甲苯磺酸 、 sodium hydroxide 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 60.5h， 生成 3α,7α,16β-trihydroxy-6α-ethyl-5β-cholan-24-oic acid sodium salt
  参考文献：
  名称：

  Avicholic Acid: A Lead Compound from Birds on the Route to Potent TGR5 Modulators

  摘要：

  Grounding on our former 3D QSAR studies, a knowledge-based screen of natural bile acids from diverse animal species has led to the identification of avicholic acid as a selective but weak TGRS agonist. Chemical modifications of this compound resulted in the disclosure of 6 alpha-ethyl-16-epi-avicholic acid that shows enhanced potency at TGRS and FXR receptors. The synthesis, biological appraisals, and structure-activity relationships of this series of compounds are herein described. Moreover, a thorough physicochemical characterization of 6 alpha-ethyl-16-epi-avicholic acid as compared to naturally occurring bile acids is reported and discussed.

  DOI：

  10.1021/ml200256d

文献信息

• [EN] TGR5 MODULATORS AND METHODS OF USE THEREOF<br/>[FR] MODULATEURS DE TGR5 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：INTERCEPT PHARMACEUTICALS INC

  公开号：WO2010059859A1

  公开（公告）日：2010-05-27

  The invention relates to compounds of Formula (A): (A) or a salt, solvate, hydrate, or amino acid conjugate thereof. The compounds of formula A are TGR5 modulators useful for the prevention and treatment of disease.

  该发明涉及Formula (A)的化合物：(A)或其盐、溶剂合物、水合物或氨基酸共轭物。 Formula A的化合物是TGR5调节剂，可用于预防和治疗疾病。
• Avicholic Acid: A Lead Compound from Birds on the Route to Potent TGR5 Modulators
  作者：Roberto Pellicciari、Antimo Gioiello、Paola Sabbatini、Francesco Venturoni、Roberto Nuti、Carolina Colliva、Giovanni Rizzo、Luciano Adorini、Mark Pruzanski、Aldo Roda、Antonio Macchiarulo

  DOI：10.1021/ml200256d

  日期：2012.4.12

  Grounding on our former 3D QSAR studies, a knowledge-based screen of natural bile acids from diverse animal species has led to the identification of avicholic acid as a selective but weak TGRS agonist. Chemical modifications of this compound resulted in the disclosure of 6 alpha-ethyl-16-epi-avicholic acid that shows enhanced potency at TGRS and FXR receptors. The synthesis, biological appraisals, and structure-activity relationships of this series of compounds are herein described. Moreover, a thorough physicochemical characterization of 6 alpha-ethyl-16-epi-avicholic acid as compared to naturally occurring bile acids is reported and discussed.