24-去甲乌苏基脱氧胆酸甲酯 | 118316-16-8

• 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-去甲乌苏基脱氧胆酸甲酯
• 英文名称: methyl 3α,7β-dihydroxy-24-nor-5β-cholan-23-oate
• 英文别名: methyl 3α,7β-3,7-dihydroxy-24-nor-5β-cholan-23-oate；24-Nor Ursodeoxycholic Acid Methyl Ester；methyl (3R)-3-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]butanoate
• CAS: 118316-16-8
• 化学式: C₂₄H₄₀O₄
• 分子量: 392.579
• InChiKey: WTAVEKBGEXLMTO-UZVSRGJWSA-N

物化性质

• 熔点：
  175-177°C
• 溶解度：
  可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  24-去甲乌苏基脱氧胆酸甲酯 在 锂硼氢 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到3α,7β-dihydroxy-24-nor-5β-cholan-23-ol
  参考文献：
  名称：

  Modification on Ursodeoxycholic Acid (UDCA) Scaffold. Discovery of Bile Acid Derivatives As Selective Agonists of Cell-Surface G-Protein Coupled Bile Acid Receptor 1 (GP-BAR1)

  摘要：

  Bile acids are signaling molecules interacting with the nuclear receptor FXR and the G-protein coupled receptor 1 (GP-BAR1/TGR5). GP-BAR1 is a promising pharmacological target for the treatment of steatohepatitis, type 2 diabetes, and obesity. Endogenous bile acids and currently available semisynthetic bile acids are poorly selective toward GP-BAR1 and FXR. Thus, in the present study we have investigated around the structure of UDCA, a clinically used bile acid devoid of FXR agonist activity, to develop a large family of side chain modified 3 alpha,7 beta-dihydroxyl cholanoids that selectively activate GP-BAR1. In vivo and in vitro pharmacological evaluation demonstrated that administration of compound 16 selectively increases the expression of proglucagon 1, a GP-BAR1 target, in the small intestine, while it had no effect on FXR target genes in the liver. Further, compound 16 results in a significant reshaping of bile acid pool in a rodent model of cholestasis. These data demonstrate that UDCA is a useful scaffold to generate novel and selective steroidal ligands for GP-BAR1.

  DOI：

  10.1021/jm500889f
• 作为产物：
  描述：

  熊去氧胆酸 在 高氯酸 、 对甲苯磺酸 、 三氟乙酸酐 、 potassium hydroxide 、 sodium nitrite 作用下， 以 甲醇 、 水 、 三氟乙酸 为溶剂， 生成 24-去甲乌苏基脱氧胆酸甲酯
  参考文献：
  名称：

  [EN] CHOLANE DERIVATIVES FOR USE IN THE TREATMENT AND/OR PREVENTION OF FXR AND TGR5/GPBAR1 MEDIATED DISEASES
  [FR] DÉRIVÉS DE CHOLANE À UTILISER DANS LE TRAITEMENT ET/OU LA PRÉVENTION DE MALADIES MÉDIÉES PAR FXR ET TGR5/GPBAR1

  摘要：

  公开号：

  WO2015181275A8

文献信息

• CHOLANE DERIVATIVES FOR USE IN THE TREATMENT AND/OR PREVENTION OF FXR AND TGR5/GPBAR1 MEDIATED DISEASES
  申请人：BAR PHARMACEUTICALS S.R.L.

  公开号：US20170190731A1

  公开（公告）日：2017-07-06

  The present invention relates to compounds having cholane scaffolds of formula (I), said compounds for use in the treatment and/or prevention of FXR and TGR5/GPBAR1 mediated diseases.

  本发明涉及具有胆固醇骨架的化合物（I）的公式，所述化合物用于治疗和/或预防FXR和TGR5 / GPBAR1介导的疾病。
• Cholane derivatives for use in the treatment and/or prevention of FXR and TGR5/GPBAR1 mediated diseases
  申请人：BAR PHARMACEUTICALS S.R.L.

  公开号：US10407462B2

  公开（公告）日：2019-09-10

  The present invention relates to compounds having cholane scaffolds of formula (I), said compounds for use in the treatment and/or prevention of FXR and TGR5/GPBAR1 mediated diseases.

  本发明涉及具有式（I）胆烷支架的化合物，所述化合物用于治疗和/或预防 FXR 和 TGR5/GPBAR1 介导的疾病。
• WO2023/233164
  申请人：——

  公开号：——

  公开（公告）日：——