4ξ,5-dihydroxy-5ξ-androstane-3,17-dione | 110267-65-7

• 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: 4ξ,5-dihydroxy-5ξ-androstane-3,17-dione
• 英文别名: 4ξ,5-Dihydroxy-5ξ-androstan-3,17-dion；(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
• CAS: 110267-65-7
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: MAPLEUYNDAGXIX-SOJMQHQVSA-N

物化性质

• 熔点：
  218-220 °C(Solv: ethanol (64-17-5))
• 沸点：
  468.5±45.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  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
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4ξ,5-dihydroxy-5ξ-androstane-3,17-dione 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 福美司坦
  参考文献：
  名称：

  An Improved Preparation of Aromatase Inhibitor 4-Hydroxyandrost-4-ene-3,17-dione

  摘要：

  The title compound has been prepared in 47% overall yield from androst-4-ene-3,17-dione (1) by a two-step sequence comprising hydrox-ylation of 1 with OsO4 / H2O2, followed by dehydration of the resultant diols 3 in alkaline medium.

  DOI：

  10.1080/00397919208021325
• 作为产物：
  描述：

  雄烯二酮 在 四氧化锇 、 双氧水 作用下， 以 叔丁醇 为溶剂， 反应 72.0h， 生成 4ξ,5-dihydroxy-5ξ-androstane-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

文献信息

• 466. Experiments on the synthesis of substances related to the sterols. Part LIV. Degradative and synthetical studies on the A-ring of androst-4-ene-3 : 17-dione
  作者：M. J. Temple Robinson

  DOI：10.1039/jr9580002311

  日期：——