4-[3-(4-Methoxy-phenyl)-3-oxo-1-phenyl-propyl]-3,4-dihydro-1H-benzo[b]azepine-2,5-dione | 1027566-92-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-[3-(4-Methoxy-phenyl)-3-oxo-1-phenyl-propyl]-3,4-dihydro-1H-benzo[b]azepine-2,5-dione
• 英文别名: 4-[3-(4-methoxyphenyl)-3-oxo-1-phenylpropyl]-3,4-dihydro-1H-1-benzazepine-2,5-dione
• CAS: 1027566-92-2
• 化学式: C₂₆H₂₃NO₄
• 分子量: 413.473
• InChiKey: XPOAJDMPQGGZPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[3-(4-Methoxy-phenyl)-3-oxo-1-phenyl-propyl]-3,4-dihydro-1H-benzo[b]azepine-2,5-dione 在 乙酸铵 、 ammonium ferric sulfate dodecahydrate 、 三溴化硼 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 2-(4-Hydroxy-phenyl)-4-phenyl-5,7-dihydro-1,7-diaza-dibenzo[a,c]cyclohepten-6-one
  参考文献：
  名称：

  d-Fused [1]Benzazepines with Selective in Vitro Antitumor Activity:  Synthesis and Structure−Activity Relationships

  摘要：

  The synthesis of novel quinolino[3,2-d][1]benzazepines and pyrido[3,2-d][1]benzazepines is described. The in vitro antitumor activity of the compounds has been tested in the antitumor screening of the National Cancer Institute (NCI). Several 2,4-diarylpyrido[3,2-d][1]benzazepin-6-ones and -thiones turned out to exhibit considerable cytotoxicity for tumor cells. For studies of SAR within these series, substituents were introduced into the aromatic rings of the parent systems. Compounds from the thiolactam series tended to show higher potency than the corresponding lactams. Prominent compounds with noteworthy activity and remarkable selectivity for renal cancer cell lines are the lactams 10c, 10g, and 10h and the corresponding thiolactams 11c, 11g, and 11h. Methylation of the azepine nitrogen leads to complete loss of activity, whereas annelation of a triazolo ring at the lactam site or transformation of the thiolactam function to a thiolactim ether results in decreased antitumor activity and selectivity. Consequently, the secondary lactam or thiolactam structure of the seven-membered ring has to be regarded as essential for selective antitumor activity.

  DOI：

  10.1021/jm970675l
• 作为产物：
  描述：

  1H-[1]-苯并氮杂卓-2,5(3H,4H)-二酮 、 (2E)-1-(4-甲氧基苯基)-3-苯基-2-丙烯-1-酮 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 4-[3-(4-Methoxy-phenyl)-3-oxo-1-phenyl-propyl]-3,4-dihydro-1H-benzo[b]azepine-2,5-dione
  参考文献：
  名称：

  d-Fused [1]Benzazepines with Selective in Vitro Antitumor Activity:  Synthesis and Structure−Activity Relationships

  摘要：

  The synthesis of novel quinolino[3,2-d][1]benzazepines and pyrido[3,2-d][1]benzazepines is described. The in vitro antitumor activity of the compounds has been tested in the antitumor screening of the National Cancer Institute (NCI). Several 2,4-diarylpyrido[3,2-d][1]benzazepin-6-ones and -thiones turned out to exhibit considerable cytotoxicity for tumor cells. For studies of SAR within these series, substituents were introduced into the aromatic rings of the parent systems. Compounds from the thiolactam series tended to show higher potency than the corresponding lactams. Prominent compounds with noteworthy activity and remarkable selectivity for renal cancer cell lines are the lactams 10c, 10g, and 10h and the corresponding thiolactams 11c, 11g, and 11h. Methylation of the azepine nitrogen leads to complete loss of activity, whereas annelation of a triazolo ring at the lactam site or transformation of the thiolactam function to a thiolactim ether results in decreased antitumor activity and selectivity. Consequently, the secondary lactam or thiolactam structure of the seven-membered ring has to be regarded as essential for selective antitumor activity.

  DOI：

  10.1021/jm970675l