7β-hydroxy-5β-cholan-24-oic acid | 10601-78-2

• 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
• 英文名称: 7β-hydroxy-5β-cholan-24-oic acid
• 英文别名: 7β-Hydroxycholanic Acid；7beta-Hydroxy-5beta-cholan-24-oic Acid；(4R)-4-[(5S,7S,8R,9S,10S,13R,14S,17R)-7-hydroxy-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: 10601-78-2
• 化学式: C₂₄H₄₀O₃
• 分子量: 376.58
• InChiKey: JVMCMMXFADJQKU-KEUPPCRPSA-N

物化性质

• 沸点：
  511.1±23.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  牛磺酸 、 7β-hydroxy-5β-cholan-24-oic acid 在 三乙胺 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.17h， 以27%的产率得到7β-hydroxy-5β-cholan-24-oyl taurine sodium
  参考文献：
  名称：

  Exploitation of Cholane Scaffold for the Discovery of Potent and Selective Farnesoid X Receptor (FXR) and G-Protein Coupled Bile Acid Receptor 1 (GP-BAR1) Ligands

  摘要：

  Nuclear and G-protein coupled receptors are considered major targets for drug discovery. FXR and GP-BAR1, two bile acid-activated receptors, have gained increasing consideration as druggable receptors. Because endogenous bile acids often target both receptor families, the development of selective ligands has been proven difficult, exposing patients to side effects linked to an unwanted activation of one of the two receptors. In the present study, we describe a novel library of semisynthetic bile acid derivatives obtained by modifications on the cholane scaffold. The pharmacological characterization of this library led to the discovery of 7a-hydroxy-5 beta-cholan-24-sulfate (7), 6 beta-ethyl-3a,7 beta-dihydroxy-5 beta-cholan-24-ol (EUDCOH, 26), and 6a-ethyl-3a, 7a-dihydroxy-24-nor-5 beta-cholan-23-ol (NorECDCOH, 30) as novel ligands for FXR and GP-BAR1 that might hold utility in the treatment of FXR and GP-BAR1 mediated disorders.

  DOI：

  10.1021/jm501273r
• 作为产物：
  描述：

  Methyl 7α-(Mesyloxy)cholanate 在 18-冠醚-6 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以57%的产率得到7β-hydroxy-5β-cholan-24-oic acid
  参考文献：
  名称：

  Potential bile acid metabolites. 8. 7,12-Dihydroxy- and 7.beta.-hydroxy-5.beta.-cholanic acids

  摘要：

  DOI：

  10.1021/jo00156a010

文献信息

• Process for the enzymatic regeneration of redox cofactors
  申请人：ANNIKKI GMBH

  公开号：US11339415B2

  公开（公告）日：2022-05-24

  A process for the enzymatic regeneration of the redox cofactors NAD+/NADH and NADP+/NADPH in a one-pot reaction, wherein, as a result of at least two further enzymatically catalyzed redox reactions proceeding in the same reaction batch (product-forming reactions), one of the two redox cofactors accumulates in its reduced form and, respectively, the other one in its oxidized form, characterized in that a) in the regeneration reaction which reconverts the reduced cofactor into its original oxidized form, oxygen or a compound of general formula R1C(O)COOH is reduced, and b) in the regeneration reaction which reconverts the oxidized cofactor into its original reduced form, a compound of general formula R2CH(OH)R3 is oxidized and wherein R1, R2 and R3 in the compounds have different meanings.

  一种在单锅反应中用酶再生氧化还原辅助因子 NAD+/NADH 和 NADP+/NADPH 的工艺，其中，由于在同一批反应（生成物反应）中进行了至少两个酶催化的氧化还原反应，两种氧化还原辅助因子中的一种以其还原形式积累，另一种分别以其氧化形式积累、其特征在于：a) 在将还原型辅助因子重新转化为原始氧化型的再生反应中，氧或通式 R1C(O)COOH 的化合物被还原；b) 在将氧化型辅助因子重新转化为原始还原型的再生反应中，通式 R2CH(OH)R3 的化合物被氧化，其中化合物中的 R1、R2 和 R3 具有不同的含义。
• METHODS AND COMPOSITIONS FOR TREATING VARIOUS DISORDERS
  申请人：Amylyx Pharmaceuticals, Inc.

  公开号：US20220152058A1

  公开（公告）日：2022-05-19

  Provided herein are methods and compositions for treating at least one symptom of ALS, slowing ALS disease progression, or reducing the deterioration of one or more bodily functions affected by ALS in a subject. The methods can include administering to the subject a bile acid or a pharmaceutically acceptable salt thereof and a phenylbutyrate compound.
• Exploitation of Cholane Scaffold for the Discovery of Potent and Selective Farnesoid X Receptor (FXR) and G-Protein Coupled Bile Acid Receptor 1 (GP-BAR1) Ligands
  作者：Carmen Festa、Barbara Renga、Claudio D’Amore、Valentina Sepe、Claudia Finamore、Simona De Marino、Adriana Carino、Sabrina Cipriani、Maria Chiara Monti、Angela Zampella、Stefano Fiorucci

  DOI：10.1021/jm501273r

  日期：2014.10.23

  Nuclear and G-protein coupled receptors are considered major targets for drug discovery. FXR and GP-BAR1, two bile acid-activated receptors, have gained increasing consideration as druggable receptors. Because endogenous bile acids often target both receptor families, the development of selective ligands has been proven difficult, exposing patients to side effects linked to an unwanted activation of one of the two receptors. In the present study, we describe a novel library of semisynthetic bile acid derivatives obtained by modifications on the cholane scaffold. The pharmacological characterization of this library led to the discovery of 7a-hydroxy-5 beta-cholan-24-sulfate (7), 6 beta-ethyl-3a,7 beta-dihydroxy-5 beta-cholan-24-ol (EUDCOH, 26), and 6a-ethyl-3a, 7a-dihydroxy-24-nor-5 beta-cholan-23-ol (NorECDCOH, 30) as novel ligands for FXR and GP-BAR1 that might hold utility in the treatment of FXR and GP-BAR1 mediated disorders.
• Potential bile acid metabolites. 8. 7,12-Dihydroxy- and 7.beta.-hydroxy-5.beta.-cholanic acids
  作者：Takashi Iida、Frederic C. Chang

  DOI：10.1021/jo00156a010

  日期：1983.4