4β,5α-dihydroxyandrostane-3,17-dione

• 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: 4β,5α-dihydroxyandrostane-3,17-dione
• 英文别名: (4R,5S,8R,9S,10R,13S,14S)-4,5-dihydroxy-10,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: MAPLEUYNDAGXIX-MOZDRDNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  福美司坦 在 dipotassium hydrogenphosphate 、 葡萄糖 、 sodium chloride 作用下， 以 丙酮 为溶剂， 反应 120.0h， 以86 mg的产率得到4β,5α-dihydroxyandrostane-3,17-dione
  参考文献：
  名称：

  Synthesis and Bioconversions of Formestane

  摘要：

  In an effort to generate new steroidal aromatase inhibitors, formestane (4-hydroxyandrost-4-ene-3,17-dione) (1) was biotransformed by Rhizopus oryzae to yield the known 4 beta,5 alpha-dihydroxyandrostane-3,17-dione as the major product (5) and bioconverted by Beauveria bassiana to afford the known reduced 4,17 beta-dihydroxyandrost-4-en-3-one (6) and 3 alpha,17 beta-dihydroxy-5 beta-androstan-4-one (7) and the new 4,11 alpha,17 beta-trihydroxyandrost-4-en-3-one (8). All the metabolites showed more potent activities than their parent congener in the aromatase and MCF-7 breast cancer assays. The bioactivities and structural elucidation of these metabolites as well as the semisynthesis of formestane (1) from testosterone (2) are reported herein.

  DOI：

  10.1021/np400585t