1,1,15,15-tetrakis(4'-methoxyphenyl)-2,14-diphenyl-1,14-pentadecadiene | 251663-30-6

• 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: 1,1,15,15-tetrakis(4'-methoxyphenyl)-2,14-diphenyl-1,14-pentadecadiene
• CAS: 251663-30-6
• 化学式: C₅₅H₆₀O₄
• 分子量: 785.079
• InChiKey: YQFZJONSKABKPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.63
• 重原子数：
  59.0
• 可旋转键数：
  22.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,1,15,15-tetrakis(4'-methoxyphenyl)-2,14-diphenyl-1,14-pentadecadiene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到1,1,15,15-tetrakis(4'-hydroxyphenyl)-2,14-diphenyl-1,14-pentadecadiene
  参考文献：
  名称：

  Synthesis and Preliminary in Vitro Cytotoxic Activity of New Triphenylethylene Dimers

  摘要：

  We have synthesized a series of six nonsteroidal homo- and heterobifunctional estrogenic dimers designed for the treatment of breast cancer. They are made of two triphenylethylene moieties linked by an aliphatic chain. The synthesis used six steps, from the known alcohol 5, with an overall yield of more than 60%. This article describes the synthesis of these products and their in vitro biological activity on two human breast cancer cell lines: MCF-7 and MDA-MB-231. The dimers are generally less active than tamoxifen, which presents an IC50 = 16 and 40 mu M on MCF-7 and MDA-MB-231 cell lines, respectively. However, the symmetrical dimer bearing six hydroxy functions possesses the best in vitro cytotoxic activity of the series, showing an IC50 = 38 mu M on both types of cells. It was observed that the cytotoxicity of the dimers increases with the number of hydroxy groups present on the aromatic rings. (C) 1999 Academic Press.

  DOI：

  10.1006/bioo.1999.1141
• 作为产物：
  描述：

  1,15,15-tris(4'-methoxyphenyl)-2,14-diphenyl-14-pentadecen-1-one 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 5.0h， 生成 1,1,15,15-tetrakis(4'-methoxyphenyl)-2,14-diphenyl-1,14-pentadecadiene
  参考文献：
  名称：

  Synthesis and Preliminary in Vitro Cytotoxic Activity of New Triphenylethylene Dimers

  摘要：

  We have synthesized a series of six nonsteroidal homo- and heterobifunctional estrogenic dimers designed for the treatment of breast cancer. They are made of two triphenylethylene moieties linked by an aliphatic chain. The synthesis used six steps, from the known alcohol 5, with an overall yield of more than 60%. This article describes the synthesis of these products and their in vitro biological activity on two human breast cancer cell lines: MCF-7 and MDA-MB-231. The dimers are generally less active than tamoxifen, which presents an IC50 = 16 and 40 mu M on MCF-7 and MDA-MB-231 cell lines, respectively. However, the symmetrical dimer bearing six hydroxy functions possesses the best in vitro cytotoxic activity of the series, showing an IC50 = 38 mu M on both types of cells. It was observed that the cytotoxicity of the dimers increases with the number of hydroxy groups present on the aromatic rings. (C) 1999 Academic Press.

  DOI：

  10.1006/bioo.1999.1141