methyl 3α,7α-dihydroxy-6α-methyl-5β-cholan-24-oate | 951694-71-6

• 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: methyl 3α,7α-dihydroxy-6α-methyl-5β-cholan-24-oate
• 英文别名: methyl (4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-3,7-dihydroxy-6,10,13-trimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 951694-71-6
• 化学式: C₂₆H₄₄O₄
• 分子量: 420.633
• InChiKey: IYSKBFPWSPZFMZ-ZWECCWDJSA-N

物化性质

• 沸点：
  514.4±25.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  5
• 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：

  methyl 3α,7α-dihydroxy-6α-methyl-5β-cholan-24-oate 在 盐酸 、 sodium hydroxide 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 28.58h， 生成 6alpha,23(S)-dimethyl-Chenodeoxycholic acid
  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：

  3Α-羟基-7-氧代-5Β-胆烷酸 在 sodium tetrahydroborate 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 methyl 3α,7α-dihydroxy-6α-methyl-5β-cholan-24-oate
  参考文献：
  名称：

  6α-Ethyl-Chenodeoxycholic Acid (6-ECDCA), a Potent and Selective FXR Agonist Endowed with Anticholestatic Activity

  摘要：

  A series of 6alpha-alkyl-substituted analogues of chenodeoxycholic acid (CDCA) were synthesized and evaluated as potential farnesoid X receptor (FXR) ligands. Among them, 6alpha-ethyl-chenodeoxycholic acid (6-ECDCA) was shown to be a very potent and selective FXR agonist (EC50 = 99 nM) and to be endowed with anticholeretic activity in an in vivo rat model of cholestasis.

  DOI：

  10.1021/jm025529g