24-(2-phenethyl)-3α,7β-dihydroxy-5β-cholanamide | 1260542-94-6

• 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: 24-(2-phenethyl)-3α,7β-dihydroxy-5β-cholanamide
• 英文别名: 24-Phenethyl-3alpha,7beta-dihydroxy-5beta-cholanamide；(4R)-4-[(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]-N-(2-phenylethyl)pentanamide
• CAS: 1260542-94-6
• 化学式: C₃₂H₄₉NO₃
• 分子量: 495.746
• InChiKey: MHVKIFFTUGYXIJ-BFIYFSNLSA-N

物化性质

• 熔点：
  100-103 °C
• 沸点：
  667.7±40.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  熊去氧胆酸 在 氯化亚砜 、 高氯酸 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 24-(2-phenethyl)-3α,7β-dihydroxy-5β-cholanamide
  参考文献：
  名称：

  Ursodeoxycholic Acid Amides As Novel Glucocorticoid Receptor Modulators

  摘要：

  Ursodeoxycholic acid (UDCA) is used for the treatment of hepatic inflammatory diseases Recent studies have shown that UDCA's biological effects are partly glucocorticoid receptor (GR) mediated UDCA derivatives were synthesized and screened for ability to induce GR translocation in a high content analysis assay using the esophageal cancel SKGT-4 cell line UDCA derivatives induced GR translocation in a time dependent manner with equal efficacy to that of dexamethasone (Dex) and with greatly increased potency relative to UDCA The cyclopropylamide la suppressed TNF-alpha Induced NF-kappa B activity and it induced GRE transactivation la was unable to displace Dex from the GR ligand binding domain (LBD) in a competition experiment but was capable of coactivator recruitment in a time-resolved fluorescence energy transfer assay (TR-FRET) This represents a novel mechanism of action for a GR modulator These derivatives could result in a new class of GR modulators

  DOI：

  10.1021/jm100860s

文献信息

• Ursodeoxycholic Acid Amides As Novel Glucocorticoid Receptor Modulators
  作者：Ruchika Sharma、David Prichard、Ferenc Majer、Anne-Marie Byrne、Dermot Kelleher、Aideen Long、John F. Gilmer

  DOI：10.1021/jm100860s

  日期：2011.1.13

  Ursodeoxycholic acid (UDCA) is used for the treatment of hepatic inflammatory diseases Recent studies have shown that UDCA's biological effects are partly glucocorticoid receptor (GR) mediated UDCA derivatives were synthesized and screened for ability to induce GR translocation in a high content analysis assay using the esophageal cancel SKGT-4 cell line UDCA derivatives induced GR translocation in a time dependent manner with equal efficacy to that of dexamethasone (Dex) and with greatly increased potency relative to UDCA The cyclopropylamide la suppressed TNF-alpha Induced NF-kappa B activity and it induced GRE transactivation la was unable to displace Dex from the GR ligand binding domain (LBD) in a competition experiment but was capable of coactivator recruitment in a time-resolved fluorescence energy transfer assay (TR-FRET) This represents a novel mechanism of action for a GR modulator These derivatives could result in a new class of GR modulators