3α,7β-dihydroxy-24-nor-5β-cholan-23-yl-23-sodium sulfate

• 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,7β-dihydroxy-24-nor-5β-cholan-23-yl-23-sodium sulfate
• 英文别名: sodium 3α,7β-dihydroxy-24-nor-5β-cholan-23-yl-23-sulfate；sodium;[(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]butyl] sulfate
• 化学式: C₂₃H₃₉O₆S*Na
• 分子量: 466.615
• InChiKey: YTXNTQLDIBISCA-RDYGPAGHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.48
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以442 mg的产率得到3α,7β-dihydroxy-24-nor-5β-cholan-23-yl-23-sodium sulfate
  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

• 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)
  作者：Valentina Sepe、Barbara Renga、Carmen Festa、Claudio D’Amore、Dario Masullo、Sabrina Cipriani、Francesco Saverio Di Leva、Maria Chiara Monti、Ettore Novellino、Vittorio Limongelli、Angela Zampella、Stefano Fiorucci

  DOI：10.1021/jm500889f

  日期：2014.9.25

  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.
• [EN] CHOLANE DERIVATIVES FOR USE IN THE TREATMENT AND/OR PREVENTION OF FXR AND TGR5/GPBAR1 MEDIATED DISEASES<br/>[FR] DÉRIVÉS DE CHOLANE À UTILISER DANS LE TRAITEMENT ET/OU LA PRÉVENTION DE MALADIES MÉDIÉES PAR FXR ET TGR5/GPBAR1
  申请人：BAR PHARMACEUTICALS S R L

  公开号：WO2015181275A8

  公开（公告）日：2016-02-18