7α-propoxy-17α-ethynylestra-1,3,5(10)-trien-3,17β-diol | 1393601-94-9

• 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: 7α-propoxy-17α-ethynylestra-1,3,5(10)-trien-3,17β-diol
• 英文别名: (7R,8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7-propoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 1393601-94-9
• 化学式: C₂₃H₃₀O₃
• 分子量: 354.489
• InChiKey: HTCXIYVQUUZCNP-AJIIZAQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对氟碘苯 、 7α-propoxy-17α-ethynylestra-1,3,5(10)-trien-3,17β-diol 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以50%的产率得到7α-propoxy-17α-(4'-fluorophenylethynyl)estra-1,3,5(10)-triene-3,17β-diol
  参考文献：
  名称：

  Novel 7α-alkoxy-17α-(4′-halophenylethynyl)estradiols as potential SPECT/PET imaging agents for estrogen receptor expressing tumours: Synthesis and binding affinity evaluation

  摘要：

  In order to develop potential radiolabelled probes for imaging estrogen receptor (ER) positive tumours, we have synthesized and characterized a series of novel 7 alpha-alkoxy-17 alpha-(4'-iodophenylethynyl)estra-1,3,5(10)-triene-3,17 beta-diols and 7 alpha-alkoxy-17 alpha-(4'-fluorophenylethynyl)estra-1,3,5(10)-triene-3,17 beta-diols. The fluoro-substituted compounds showed a higher ER binding affinity than the corresponding iodo-derivatives, where 7 alpha-methoxy- and 17 alpha-(4'-fluorophenylethynyl)estra-1,3,5(10)-triene-3,17 beta-diol showed the highest ER binding affinities (RBA = 80.9% and 78.9%, respectively), among the halophenylethynyl compounds studied and should be further explored as potential PET biomarkers for imaging of ER expressing tumours. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.05.004
• 作为产物：
  描述：

  7α-propoxyestra-1,3,5(10)-trien-3-ol-17-one-17,17-(2'-[5',5'-dimethyl-1',3'-dioxane]) 在 咪唑 、 四丁基氟化铵 、 sodium carbonate 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 43.0h， 生成 7α-propoxy-17α-ethynylestra-1,3,5(10)-trien-3,17β-diol
  参考文献：
  名称：

  Novel 7α-alkoxy-17α-(4′-halophenylethynyl)estradiols as potential SPECT/PET imaging agents for estrogen receptor expressing tumours: Synthesis and binding affinity evaluation

  摘要：

  In order to develop potential radiolabelled probes for imaging estrogen receptor (ER) positive tumours, we have synthesized and characterized a series of novel 7 alpha-alkoxy-17 alpha-(4'-iodophenylethynyl)estra-1,3,5(10)-triene-3,17 beta-diols and 7 alpha-alkoxy-17 alpha-(4'-fluorophenylethynyl)estra-1,3,5(10)-triene-3,17 beta-diols. The fluoro-substituted compounds showed a higher ER binding affinity than the corresponding iodo-derivatives, where 7 alpha-methoxy- and 17 alpha-(4'-fluorophenylethynyl)estra-1,3,5(10)-triene-3,17 beta-diol showed the highest ER binding affinities (RBA = 80.9% and 78.9%, respectively), among the halophenylethynyl compounds studied and should be further explored as potential PET biomarkers for imaging of ER expressing tumours. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.05.004