17-ethylenedioxy-3-acetoxyestra-1,3,5(10)-trien-11β-ol | 78806-49-2

• 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: 17-ethylenedioxy-3-acetoxyestra-1,3,5(10)-trien-11β-ol
• 英文别名: 11β-hydroxyestrone 17-ethyleneketal 3-acetate
• CAS: 78806-49-2
• 化学式: C₂₂H₂₈O₅
• 分子量: 372.461
• InChiKey: QDRCMIJZSXTRGI-FCMAGTKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  27.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  17-ethylenedioxy-3-acetoxyestra-1,3,5(10)-trien-11β-ol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 以80%的产率得到11-Ketoestrone 17-ethyleneketal 3-acetate
  参考文献：
  名称：

  Steroid structure and function VII. Remarkable estrogenicity of 3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione

  摘要：

  Remarkably high estrogenic activity was observed for 3-hydroxy-9 beta-estra-1,3,5(10)-triene-11,17-dione despite its unusual bent conformation. The 9 alpha epimer of this compound has markedly less activity despite the fact that its overall shape is nearly identical to that of estrone. The potency of these compounds in enhancing uterine weight in Fischer rats and reducing ovarian weight in parabiosed rats was compared with that of estrone, and the structures were unambiguously identified by X-ray crystallographic study. The results underscore the importance of the phenolic ring A to estrogenic activity, and suggest a tolerance of the putative estrogenic receptor to flexibility in overall molecular shape.

  DOI：

  10.1016/0039-128x(80)90046-x
• 作为产物：
  描述：

  乙酸酐 、 17-ethylenedioxyestra-1,3,5(10)-triene-3,11β-diol 以 吡啶 为溶剂， 反应 0.5h， 生成 17-ethylenedioxy-3-acetoxyestra-1,3,5(10)-trien-11β-ol
  参考文献：
  名称：

  Steroid structure and function VII. Remarkable estrogenicity of 3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione

  摘要：

  Remarkably high estrogenic activity was observed for 3-hydroxy-9 beta-estra-1,3,5(10)-triene-11,17-dione despite its unusual bent conformation. The 9 alpha epimer of this compound has markedly less activity despite the fact that its overall shape is nearly identical to that of estrone. The potency of these compounds in enhancing uterine weight in Fischer rats and reducing ovarian weight in parabiosed rats was compared with that of estrone, and the structures were unambiguously identified by X-ray crystallographic study. The results underscore the importance of the phenolic ring A to estrogenic activity, and suggest a tolerance of the putative estrogenic receptor to flexibility in overall molecular shape.

  DOI：

  10.1016/0039-128x(80)90046-x

文献信息

• Structure-activity relationships of four 11-hydroxyestrones isomeric at the C-9 and C-11 positions
  作者：R. Bruce Gabbard、Leslie F. Hamer、Albert Segaloff

  DOI：10.1016/s0039-128x(81)90234-8

  日期：1981.3

  The synthesis of 11 alpha-hydroxyestrone, 11 alpha-hydroxy-9 beta-estrone, and 11 beta-hydroxy-9 beta-estrone are presented. The reduction of 11-keto-9 beta-estrone 17-ethyleneketal by sodium in ethanol or sodium borohydride resulted in 11-hydroxy-9 beta-estrones. The 11-hydroxyl group configurations were opposite to expectations: sodium in boiling ethanol afforded the axial 11 beta-hydroxy-9 beta-estrone, while sodium borohydride in boiling tetrahydrofuran gave the equatorial 11 alpha-hydroxy-9 beta-estrone. In immature rat uterotropic bioassays using subcutaneous injections, 11 alpha-hydroxyestrone was 2 times as active as 11 alpha-hydroxy-9 beta-estrone, and 11 beta-hydroxyestrone was 10 times as active as 11 beta-hydroxy-9 beta-estrone.