2-(2-dimethylaminoethyl)-5-(3-methoxyphenyl)benzo[de]isoquinoline-1,3-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-dimethylaminoethyl)-5-(3-methoxyphenyl)benzo[de]isoquinoline-1,3-dione
• 英文别名: 2-[2-(Dimethylamino)ethyl]-5-(3-methoxyphenyl)benzo[de]isoquinoline-1,3-dione；2-[2-(dimethylamino)ethyl]-5-(3-methoxyphenyl)benzo[de]isoquinoline-1,3-dione
• 化学式: C₂₃H₂₂N₂O₃
• 分子量: 374.439
• InChiKey: XATHFMDNDYGQFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-dimethylaminoethyl)-5-(3-methoxyphenyl)benzo[de]isoquinoline-1,3-dione 在 三溴化硼 、 碳酸氢钠 作用下， 以 二氯甲烷 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 为溶剂， 以78%的产率得到2-(2-dimethylaminoethyl)-5-(3-hydroxyphenyl)benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Synthesis and study of antiproliferative, antitopoisomerase II, DNA-intercalating and DNA-damaging activities of arylnaphthalimides

  摘要：

  A series of arylnaphthalimides were designed and synthesized to overcome the dose-limiting cytotoxicity of N-acetylated metabolites arising from amonafide, the prototypical antitumour naphthalimide whose biomedical properties have been related to its ability to intercalate the DNA and poison the enzyme Topoisomerase II. Thus, these arylnaphthalimides were first evaluated for their antiproliferative activity against two tumour cell lines and for their antitopoisomerase II in vitro activities, together with their ability to intercalate the DNA in vitro and also through docking modelization. Then, the well-known DNA damage response in Saccharomyces cerevisiae was employed to critically evaluate whether these novel compounds can damage the DNA in vivo. By performing all these assays we conclude that the 5-arylsubstituted naphthalimides not only keep but also improve amonafide's biological activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.039
• 作为产物：
  描述：

  氨萘非特 在 四(三苯基膦)钯 、 硫酸 、 sodium carbonate 作用下， 以 乙醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 18.75h， 生成 2-(2-dimethylaminoethyl)-5-(3-methoxyphenyl)benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Synthesis and study of antiproliferative, antitopoisomerase II, DNA-intercalating and DNA-damaging activities of arylnaphthalimides

  摘要：

  A series of arylnaphthalimides were designed and synthesized to overcome the dose-limiting cytotoxicity of N-acetylated metabolites arising from amonafide, the prototypical antitumour naphthalimide whose biomedical properties have been related to its ability to intercalate the DNA and poison the enzyme Topoisomerase II. Thus, these arylnaphthalimides were first evaluated for their antiproliferative activity against two tumour cell lines and for their antitopoisomerase II in vitro activities, together with their ability to intercalate the DNA in vitro and also through docking modelization. Then, the well-known DNA damage response in Saccharomyces cerevisiae was employed to critically evaluate whether these novel compounds can damage the DNA in vivo. By performing all these assays we conclude that the 5-arylsubstituted naphthalimides not only keep but also improve amonafide's biological activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.039