3-O-benzyl-estra-1,3,5(10)-trien-3-ol-17-one-17,17-(2'-[5',5'-dimethyl-1',3'-dioxane]) | 1393601-77-8

• 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: 3-O-benzyl-estra-1,3,5(10)-trien-3-ol-17-one-17,17-(2'-[5',5'-dimethyl-1',3'-dioxane])
• CAS: 1393601-77-8
• 化学式: C₃₀H₃₈O₃
• 分子量: 446.63
• InChiKey: CDSBUQKZMFXWSB-DIBLIPFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-estra-1,3,5(10)-trien-3-ol-17-one-17,17-(2'-[5',5'-dimethyl-1',3'-dioxane]) 在 甲醇 、 sodium tetrahydroborate 、 potassium permanganate 、 lithium aluminium tetrahydride 、 sodium hydride 、 碳酸氢钠 、 对甲苯磺酸 、 2,2-二甲基-1,3-丙二醇 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 36.0h， 生成 3-O-benzyl-7α-propoxyestra-1,3,5(10)-trien-3-ol-17-one-17,17-(2'-[5',5'-dimethyl-1',3'-dioxane])
  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：

  3-O-苄基雌酮 、 2,2-二甲基-1,3-丙二醇 在 碳酸氢钠 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 1.5h， 以57%的产率得到3-O-benzyl-estra-1,3,5(10)-trien-3-ol-17-one-17,17-(2'-[5',5'-dimethyl-1',3'-dioxane])
  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