(6β,7β,8α,9β,10α,13α,14β)-6,7-epoxyandrost-4-ene-3,17-dione | 960525-68-2

• 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: (6β,7β,8α,9β,10α,13α,14β)-6,7-epoxyandrost-4-ene-3,17-dione
• 英文别名: (1S,2R,4S,10S,11R,14R,18R)-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-5-ene-7,15-dione
• CAS: 960525-68-2
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: VXUAXLOVFFOKOO-VIMBOAPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6β,7β,8α,9β,10α,13α,14β)-6,7-epoxyandrost-4-ene-3,17-dione 在 palladium on activated charcoal 氢气 作用下， 以 吡啶 为溶剂， 反应 18.0h， 以64%的产率得到(5α,7β,8α,9β,10α,13α,14β)-7-hydroxyandrostane-3,17-dione
  参考文献：
  名称：

  Synthesis, Characterization, and Receptor Interaction Profiles of Enantiomeric Bile Acids

  摘要：

  Bile acids are endogenous steroid detergents with receptor-mediated physiologic actions including activation of the G-protein coupled receptor TGR5 and gene regulation mediated by nuclear receptors. In this study, we report the first synthesis of enantiomeric lithocholic acid (ent-LCA, ent-1) and chenodeoxycholic acid (ent-CDCA, ent-2) via ent-testosterone (3). ent-1 was synthesized in 21 total steps in 4.2% yield, whereas ent-2 was obtained in 23 total steps in 0.8% yield. Critical micelle concentrations of the enantiomeric bile acids were found to be identical to their natural counterparts. Furthermore, enantiomeric bile acids were also tested for their ability to modulate bile acid activated proteins: farnesoid X receptor, vitamin D receptor, pregnane X receptor, and TGR5. Interestingly, ent-1 and ent-2 showed differential interactions with these proteins as compared to their corresponding natural bile acids. These data highlight the potential for using enantioselectivity as away to distinguish between receptor and nonreceptor-mediated functions of natural bile acids.

  DOI：

  10.1021/jm0707931
• 作为产物：
  描述：

  (8α,9β,10α,13α,14β)-androsta-4,6-diene-3,17-dione 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以58%的产率得到(6β,7β,8α,9β,10α,13α,14β)-6,7-epoxyandrost-4-ene-3,17-dione
  参考文献：
  名称：

  Synthesis, Characterization, and Receptor Interaction Profiles of Enantiomeric Bile Acids

  摘要：

  Bile acids are endogenous steroid detergents with receptor-mediated physiologic actions including activation of the G-protein coupled receptor TGR5 and gene regulation mediated by nuclear receptors. In this study, we report the first synthesis of enantiomeric lithocholic acid (ent-LCA, ent-1) and chenodeoxycholic acid (ent-CDCA, ent-2) via ent-testosterone (3). ent-1 was synthesized in 21 total steps in 4.2% yield, whereas ent-2 was obtained in 23 total steps in 0.8% yield. Critical micelle concentrations of the enantiomeric bile acids were found to be identical to their natural counterparts. Furthermore, enantiomeric bile acids were also tested for their ability to modulate bile acid activated proteins: farnesoid X receptor, vitamin D receptor, pregnane X receptor, and TGR5. Interestingly, ent-1 and ent-2 showed differential interactions with these proteins as compared to their corresponding natural bile acids. These data highlight the potential for using enantioselectivity as away to distinguish between receptor and nonreceptor-mediated functions of natural bile acids.

  DOI：

  10.1021/jm0707931

文献信息

• Synthesis, Characterization, and Receptor Interaction Profiles of Enantiomeric Bile Acids
  作者：Bryson W. Katona、Carolyn L. Cummins、Andrew D. Ferguson、Tingting Li、Daniel R. Schmidt、David J. Mangelsdorf、Douglas F. Covey

  DOI：10.1021/jm0707931

  日期：2007.11.1

  Bile acids are endogenous steroid detergents with receptor-mediated physiologic actions including activation of the G-protein coupled receptor TGR5 and gene regulation mediated by nuclear receptors. In this study, we report the first synthesis of enantiomeric lithocholic acid (ent-LCA, ent-1) and chenodeoxycholic acid (ent-CDCA, ent-2) via ent-testosterone (3). ent-1 was synthesized in 21 total steps in 4.2% yield, whereas ent-2 was obtained in 23 total steps in 0.8% yield. Critical micelle concentrations of the enantiomeric bile acids were found to be identical to their natural counterparts. Furthermore, enantiomeric bile acids were also tested for their ability to modulate bile acid activated proteins: farnesoid X receptor, vitamin D receptor, pregnane X receptor, and TGR5. Interestingly, ent-1 and ent-2 showed differential interactions with these proteins as compared to their corresponding natural bile acids. These data highlight the potential for using enantioselectivity as away to distinguish between receptor and nonreceptor-mediated functions of natural bile acids.