11-Ketoestrone 17-ethyleneketal 3-acetate | 78806-50-5

• 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: 11-Ketoestrone 17-ethyleneketal 3-acetate
• 英文别名: 3-acetoxy-17-ethylenedioxy-estra-1,3,5(10)-trien-11-one；17-ethylenedioxy-3-acetoxyestra-1,3,5(10)-trien-11-one；[(8'S,9'S,13'S,14'S)-13'-methyl-11'-oxospiro[1,3-dioxolane-2,17'-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene]-3'-yl] acetate
• CAS: 78806-50-5
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: BQHFSDFYRRGISA-MMKMLUHNSA-N

物化性质

• 沸点：
  524.9±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  11-Ketoestrone 17-ethyleneketal 3-acetate 在 氢氧化钾 、 sodium 作用下， 以 乙醇 为溶剂， 反应 0.75h， 生成 (8S,9R,11R,13S,14S)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolane]-3,11-diol
  参考文献：
  名称：

  Structure-activity relationships of four 11-hydroxyestrones isomeric at the C-9 and C-11 positions

  摘要：

  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.

  DOI：

  10.1016/s0039-128x(81)90234-8
• 作为产物：
  描述：

  3-hydroxy-estra-1,3,5(10),9(11)-tetraen-17-one 在 氢氧化钾 、 dimethyl sulfide borane 、 pyridiniumchlorochromate on aluminumoxide 、 四丁基氢氧化铵 、 双氧水 、 草酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 11-Ketoestrone 17-ethyleneketal 3-acetate
  参考文献：
  名称：

  Improved synthesis of a protected 11-oxoestrone

  摘要：

  An improved synthesis of 11-oxoestrone-3-acetate-17-ethyleneketal is reported. Adjustments are proposed for the oxidation of estrone by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone into 9(11)-dehydroestrone. A complete hydroboration-oxidation of the resulting ketal, by means of borane-methylsulfide complex, gives the corresponding 11-hydroxy derivative. This latter compound is then acetylated for successful oxidation with pyridinium chlorochromate on alumina. The overall yield is 30%.

  DOI：

  10.1016/0039-128x(95)00145-g

文献信息

• Synthesis of novel steroidal agonists, partial agonists, and antagonists for the glucocorticoid receptor
  作者：Zhuang Jin、Hua Lin、Sathish Srinivasan、Jerome C. Nwachukwu、Nelson Bruno、Patrick R. Griffin、Kendall W. Nettles、Theodore M. Kamenecka

  DOI：10.1016/j.bmcl.2016.11.007

  日期：2017.1

  glucocorticoids could be limited by developing new compounds that selectively modulate anti-inflammatory activity of the glucocorticoid receptor (GR). We have synthesized a novel series of steroidal GR ligands, including potent agonists, partial agonists and antagonists with a wide range of effects on inhibiting secretion of interleukin-6. Some of these new ligands were designed to directly impact conformational

  糖皮质激素的不良反应可通过开发选择性调节糖皮质激素受体（GR）抗炎活性的新化合物来加以限制。我们已经合成了一系列新型的甾体GR配体，包括有效的激动剂，部分激动剂和拮抗剂，这些抑制剂在抑制白介素6的分泌方面具有广泛的作用。这些新的配体中的一些被设计为直接影响GR配体结合域（LBD）中的helix-12的构象稳定性。这些化合物以与炎症反应程度成反比的方式调节GR活性和糖皮质激素诱导的基因表达。相比之下，旨在直接调节helix-12外部的LBD表位的化合物导致GR介导的基因表达和炎症反应的解离水平。所以，
• Steroid structure and function VII. Remarkable estrogenicity of 3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione
  作者：Albert Segaloff、R.Bruce Gabbard、Albert Flores、Ronald F. Borne、John K. Baker、William L. Duax、Phyllis D. Strong、Douglas C. Rohrer

  DOI：10.1016/0039-128x(80)90046-x

  日期：1980.3

  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.