7,8-bis(4-hydroxyphenyl)-N-methyl-N-[3-(4,4,5,5,5-pentafluoropentylsulfanyl)propyl]dec-7-enamide | 752221-92-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 7,8-bis(4-hydroxyphenyl)-N-methyl-N-[3-(4,4,5,5,5-pentafluoropentylsulfanyl)propyl]dec-7-enamide
• CAS: 752221-92-4
• 化学式: C₃₁H₄₀F₅NO₃S
• 分子量: 601.722
• InChiKey: DCALXNYNUMWTFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.93
• 重原子数：
  41.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  60.77
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7,8-bis(4-hydroxyphenyl)-N-methyl-N-[3-(4,4,5,5,5-pentafluoropentylsulfanyl)propyl]dec-7-enamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-[4-(4-hydroxyphenyl)-10-[methyl-[3-(4,4,5,5,5-pentafluoropentylsulfanyl)propyl]amino]dec-3-en-3-yl]phenol
  参考文献：
  名称：

  Synthesis and biological evaluation of stilbene-based pure estrogen antagonists

  摘要：

  Replacement of one of the ethyl substituents in diethylstilbestrol by side chains with functional groups converted this potent estrogen into pure antiestrogens with the potential for the treatment of breast cancer. These agents completely suppressed estrogen receptor-mediated gene activation and inhibited the growth of estrogen-sensitive MCF-7 breast cancer cells in submicromolar concentrations. The most potent derivative displayed similar activity as fulvestrant (ICI 182,780) in vitro and in the mouse uterine weight test. Obviously, the stilbene structure can act as a substitute for estradiol in the development of pure estrogen antagonists. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.098
• 作为产物：
  描述：

  6-溴己酸乙酯 在 氢氧化钾 、 三溴化硼 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 7,8-bis(4-hydroxyphenyl)-N-methyl-N-[3-(4,4,5,5,5-pentafluoropentylsulfanyl)propyl]dec-7-enamide
  参考文献：
  名称：

  Synthesis and biological evaluation of stilbene-based pure estrogen antagonists

  摘要：

  Replacement of one of the ethyl substituents in diethylstilbestrol by side chains with functional groups converted this potent estrogen into pure antiestrogens with the potential for the treatment of breast cancer. These agents completely suppressed estrogen receptor-mediated gene activation and inhibited the growth of estrogen-sensitive MCF-7 breast cancer cells in submicromolar concentrations. The most potent derivative displayed similar activity as fulvestrant (ICI 182,780) in vitro and in the mouse uterine weight test. Obviously, the stilbene structure can act as a substitute for estradiol in the development of pure estrogen antagonists. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.098

文献信息

• Synthesis and biological evaluation of stilbene-based pure estrogen antagonists
  作者：Georg Walter、Renate Liebl、Erwin von Angerer

  DOI：10.1016/j.bmcl.2004.06.098

  日期：2004.9

  Replacement of one of the ethyl substituents in diethylstilbestrol by side chains with functional groups converted this potent estrogen into pure antiestrogens with the potential for the treatment of breast cancer. These agents completely suppressed estrogen receptor-mediated gene activation and inhibited the growth of estrogen-sensitive MCF-7 breast cancer cells in submicromolar concentrations. The most potent derivative displayed similar activity as fulvestrant (ICI 182,780) in vitro and in the mouse uterine weight test. Obviously, the stilbene structure can act as a substitute for estradiol in the development of pure estrogen antagonists. (C) 2004 Elsevier Ltd. All rights reserved.