methyl (4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6,10,13-trimethyl-3,7-bis(oxan-2-yloxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate | 951694-76-1

• 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: methyl (4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6,10,13-trimethyl-3,7-bis(oxan-2-yloxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 951694-76-1
• 化学式: C₃₆H₆₀O₆
• 分子量: 588.869
• InChiKey: DQTKRJUTWVGVGZ-OVDYTHGESA-N

物化性质

• 沸点：
  633.2±55.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6,10,13-trimethyl-3,7-bis(oxan-2-yloxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.33h， 生成 methyl 3α,7α-dihydroxy-6α,23-dimethyl-5β-cholan-24-oate
  参考文献：
  名称：

  Nongenomic Actions of Bile Acids. Synthesis and Preliminary Characterization of 23- and 6,23-Alkyl-Substituted Bile Acid Derivatives as Selective Modulators for the G-Protein Coupled Receptor TGR5

  摘要：

  23-Alkyl-substituted and 6,23-alkyl-disubstituted derivatives of chenodeoxvcholic acid are identified as potent and selective agonists of TGR5, a G-protein coupled receptor for bile acids (BAs). In particular. we show that methylation at the C-23(S) position of natural BAs confers a marked selectivity for TGR5 over FXR, while the 6 alpha-alkyl substitution increases the potency at both receptors. The present results allow for the first time a pharmacological differentiation of genomic versus nongenornic effects mediated by BA derivatives.

  DOI：

  10.1021/jm070633p
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 methyl 3α,7α-dihydroxy-6α-methyl-5β-cholan-24-oate 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.25h， 以90%的产率得到methyl (4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6,10,13-trimethyl-3,7-bis(oxan-2-yloxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
  参考文献：
  名称：

  Nongenomic Actions of Bile Acids. Synthesis and Preliminary Characterization of 23- and 6,23-Alkyl-Substituted Bile Acid Derivatives as Selective Modulators for the G-Protein Coupled Receptor TGR5

  摘要：

  23-Alkyl-substituted and 6,23-alkyl-disubstituted derivatives of chenodeoxvcholic acid are identified as potent and selective agonists of TGR5, a G-protein coupled receptor for bile acids (BAs). In particular. we show that methylation at the C-23(S) position of natural BAs confers a marked selectivity for TGR5 over FXR, while the 6 alpha-alkyl substitution increases the potency at both receptors. The present results allow for the first time a pharmacological differentiation of genomic versus nongenornic effects mediated by BA derivatives.

  DOI：

  10.1021/jm070633p