(2S)-(E)-4-{4-[2-(dimethylamino)ethoxy]phenyl}-3,4-diphenyl-3-buten-2-ol

• 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: (2S)-(E)-4-{4-[2-(dimethylamino)ethoxy]phenyl}-3,4-diphenyl-3-buten-2-ol
• 英文别名: S-(-)-α-hydroxytamoxifen；(E,2S)-4-[4-[2-(dimethylamino)ethoxy]phenyl]-3,4-diphenylbut-3-en-2-ol
• 化学式: C₂₆H₂₉NO₂
• 分子量: 387.522
• InChiKey: BPHFBQJMFWCHGH-DDJBQFQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  α-hydroxytamoxifen 在 吡啶 、 sodium ethanolate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (2S)-(E)-4-{4-[2-(dimethylamino)ethoxy]phenyl}-3,4-diphenyl-3-buten-2-ol
  参考文献：
  名称：

  Resolution of α-Hydroxytamoxifen; R-Isomer Forms More DNA Adducts in Rat Liver Cells

  摘要：

  The genotoxic tamoxifen metabolite alpha -hydroxytamoxifen has been resolved into R- and S-enantiomers. This was achieved by preparing its ester with S-camphanic acid, chromatographic separation into two diastereoisomers, and hydrolysis to give (+)- and (-)-alpha -hydroxytamoxifen. The configuration of the (-)-isomer was shown to be S- by degradation of an ester to a derivative of (-)-2-hydroxy-1-phenyl-1-propanone, which has already been shown to have S-configuration. Metabolism of tamoxifen by rat liver microsomes gave equal amounts of the two enantiomers. They have the same chemical properties but, on treatment of rat hepatocytes in culture, R-(+)-alpha -hydroxytamoxifen gave at least eight times as many DNA adducts as the S-(-)-isomer.

  DOI：

  10.1021/tx010027b

文献信息

• Resolution of α-Hydroxytamoxifen; R-Isomer Forms More DNA Adducts in Rat Liver Cells
  作者：Martin R. Osborne、Alan Hewer、David H. Phillips

  DOI：10.1021/tx010027b

  日期：2001.7.1

  The genotoxic tamoxifen metabolite alpha -hydroxytamoxifen has been resolved into R- and S-enantiomers. This was achieved by preparing its ester with S-camphanic acid, chromatographic separation into two diastereoisomers, and hydrolysis to give (+)- and (-)-alpha -hydroxytamoxifen. The configuration of the (-)-isomer was shown to be S- by degradation of an ester to a derivative of (-)-2-hydroxy-1-phenyl-1-propanone, which has already been shown to have S-configuration. Metabolism of tamoxifen by rat liver microsomes gave equal amounts of the two enantiomers. They have the same chemical properties but, on treatment of rat hepatocytes in culture, R-(+)-alpha -hydroxytamoxifen gave at least eight times as many DNA adducts as the S-(-)-isomer.