benzyl 3α,7α-dihydroxy-6-ethyliden-5β-cholan-24-oate | 1352328-67-6

• 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: benzyl 3α,7α-dihydroxy-6-ethyliden-5β-cholan-24-oate
• 英文别名: Benzyl 3-,7-dihydroxy-6-ethyliden-5-cholan-24-oate；benzyl (4R)-4-[(3R,5R,7S,8S,9S,10R,13R,14S,17R)-6-ethylidene-3,7-dihydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 1352328-67-6
• 化学式: C₃₃H₄₈O₄
• 分子量: 508.742
• InChiKey: QAOWMCYCZWQNGW-MUVOKEOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  benzyl 3α,7α-dihydroxy-6-ethyliden-5β-cholan-24-oate 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以95%的产率得到3α,7α-dihydroxy-6α-ethyl-5β-cholanic acid benzyl ester
  参考文献：
  名称：

  一种制备奥贝胆酸中间体及奥贝胆酸的方法

  摘要：

  本发明公开了一种制备奥贝胆酸中间体及奥贝胆酸的方法，中间体的合成路线为：本发明的奥贝胆酸中间体，在反应的过程中具有很好的立体选择性，极大地简化了奥贝胆酸的合成难度，降低了奥贝胆酸的合成成本。本发明的反应条件温和，工业上易于实现，可以得到低杂质的奥贝胆酸中间体及奥贝胆酸。本发明使用的原料安全，成本低廉，有效降低了生产成本。

  公开号：

  CN108191939A
• 作为产物：
  描述：

  benzyl 3α-hydroxy-6-ethylidene-5β-cholanoate 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以95%的产率得到benzyl 3α,7α-dihydroxy-6-ethyliden-5β-cholan-24-oate
  参考文献：
  名称：

  Conicasterol E, a Small Heterodimer Partner Sparing Farnesoid X Receptor Modulator Endowed with a Pregnane X Receptor Agonistic Activity, from the Marine Sponge Theonella swinhoei

  摘要：

  We report the isolation and pharmacological characterization of conicasterol E isolated from the marine sponge Theonella swinhoei. Pharmacological characterization of this steroid in comparison to CDCA, a natural FXR ligand, and 6-ECDCA, a synthetic FXR agonist generated by an improved synthetic strategy, and rifaximin, a potent PXR agonist, demonstrated that conicasterol E is an FXR modulator endowed with PXR agonistic activity. Conicasterol E induces the expression of genes involved in bile acids detoxification without effect on the expression of small heterodimer partner (SHP), thus sparing the expression of genes involved in bile acids biosynthesis. The relative positioning in the ligand binding domain of FXR, explored through docking calculations, demonstrated a different spatial arrangement for conicasterol E and pointed to the presence of simultaneous and efficient interactions with the receptor. In summary, conicasterol E represents a FXR modulator and PXR agonist that might hold utility in treatment of liver disorders.

  DOI：

  10.1021/jm201004p