7-丙基-鹅去氧胆酸 | 124729-58-4

• 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: 7-丙基-鹅去氧胆酸
• 中文别名: β-D-吡喃葡萄糖基-(1-&gt3)-β-D-吡喃葡萄糖基-(1-&gt3)-β-D-吡喃葡萄糖基-(1-&gt3)-β-D-吡喃葡萄糖基-(1-&gt3)-β-D-吡喃葡萄糖基-(1-&gt3)-β-D-吡喃葡萄糖基-(1-&gt3)-D-葡萄糖
• 英文名称: 3α,7α-dihydroxy-7β-n-propyl-5β-cholanoic acid
• 英文别名: 3α,7α-dihydroxy-7β-propyl-5β-cholan-24-oic acid；7beta-Propylchenodeoxycholic acid；3α,7α-dihydroxy-7β-propyl-5β-cholanoic acid；3,7-Dihydroxy-7-n-propylcholanoic acid；(4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-7-propyl-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 124729-58-4
• 化学式: C₂₇H₄₆O₄
• 分子量: 434.66
• InChiKey: BOJLONLMSDGVHC-WCEAYCHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3α-羟基-7-氧代-胆烷酸-24-甲酯 在 氢氧化钾 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 7-丙基-鹅去氧胆酸
  参考文献：
  名称：

  Synthesis of bile acid analogs: 7-alkylated chenodeoxycholic acids

  摘要：

  This paper describes a method for the preparation of 7-alkylated chenodeoxycholic acids from 3 alpha-hydroxy-7-oxo-5 beta-cholanoic acid. The synthetic procedure is based upon a Grignard reaction between the keto bile acid and an alkyl magnesium halide. Under the conditions employed, the introduction of alkyl groups is highly stereoselective. Only 7 beta-alkylated epimers are obtained. The overall yield is several-fold higher than that obtained by the previous method, which involved the preparation of an oxazoline intermediate.

  DOI：

  10.1016/0039-128x(89)90148-7

文献信息

• (E)-7-Ethylidene-lithocholic Acid (7-ELCA) Is a Potent Dual Farnesoid X Receptor (FXR) Antagonist and GPBAR1 Agonist Inhibiting FXR-Induced Gene Expression in Hepatocytes and Stimulating Glucagon-like Peptide-1 Secretion From Enteroendocrine Cells
  作者：Alzbeta Stefela、Miroslav Kaspar、Martin Drastik、Thales Kronenberger、Stanislav Micuda、Martin Dracinsky、Blanka Klepetarova、Eva Kudova、Petr Pavek

  DOI：10.3389/fphar.2021.713149

  日期：——

  Bile acids (BAs) are key signaling steroidal molecules that regulate glucose, lipid, and energy homeostasis via interactions with the farnesoid X receptor (FXR) and G-protein bile acid receptor 1 (GPBAR1). Extensive medicinal chemistry modifications of the BA scaffold led to the discovery of potent selective or dual FXR and GPBAR1 agonists. Herein, we discovered 7-ethylidene-lithocholic acid (7-ELCA)

  胆汁酸 (BA) 是关键的信号甾体分子，通过与法尼醇 X 受体 (FXR) 和 G 蛋白胆汁酸受体 1 (GPBAR1) 的相互作用来调节葡萄糖、脂质和能量稳态。BA 支架的广泛药物化学修饰导致发现了有效的选择性或双重 FXR 和 GPBAR1 激动剂。在此，我们发现 7-亚乙基-石胆酸 (7-ELCA) 作为一种新型复合 FXR 拮抗剂/GPBAR1 激动剂 (IC50 = 15 μM/EC50 = 26 nM)，在 7-烷基取代衍生物库中没有脱靶激活BA。7-ELCA 显着抑制 FXR 激动剂奥贝胆酸在人肝细胞 BSEP 和 SHP 调节中的作用。重要的是，7-ELCA 显着刺激胰高血糖素样肽-1 (GLP-1) 的产生，一种在肠内分泌细胞中对餐后葡萄糖利用具有促胰岛素作用的肠促胰岛素。我们可以认为 7-ELCA 可能是治疗 II 型糖尿病的前瞻性方法，因为 GPBAR1 和 FXR
• US4962099A
  申请人：——

  公开号：US4962099A

  公开（公告）日：1990-10-09
• Synthesis of bile acid analogs: 7-alkylated chenodeoxycholic acids
  作者：Mizuho Une、Katsumi Yamanaga、Erwin H. Mosbach、Syoji Kuroki、Takahiko Hoshita

  DOI：10.1016/0039-128x(89)90148-7

  日期：1989.1

  This paper describes a method for the preparation of 7-alkylated chenodeoxycholic acids from 3 alpha-hydroxy-7-oxo-5 beta-cholanoic acid. The synthetic procedure is based upon a Grignard reaction between the keto bile acid and an alkyl magnesium halide. Under the conditions employed, the introduction of alkyl groups is highly stereoselective. Only 7 beta-alkylated epimers are obtained. The overall yield is several-fold higher than that obtained by the previous method, which involved the preparation of an oxazoline intermediate.