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

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(2-dimethylaminoethyl)-5-iodobenzo[de]isoquinoline-1,3-dione
• 英文别名: 2-(2-(dimethylamino)ethyl)-5-iodo-1H-benzo[de]isoquinoline-1,3-(2H)-dione；2-[2-(Dimethylamino)ethyl]-5-iodobenzo[de]isoquinoline-1,3-dione；2-[2-(dimethylamino)ethyl]-5-iodobenzo[de]isoquinoline-1,3-dione
• 化学式: C₁₆H₁₅IN₂O₂
• 分子量: 394.212
• InChiKey: PUAGMRYTVMYQHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  氨萘非特	amonafide	69408-81-7	C16H17N3O2	283.33
  米托萘胺	mitonafide	54824-17-8	C16H15N3O4	313.313

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-(2-(dimethylamino)ethyl)-5-(4-hydroxyphenyl)ethynyl-1Hbenzo[de]isoquinoline-1,3-(2H)-dione	——	C24H20N2O3	384.434
  ——	5-phenyl-2-[2-(dimethylamino)ethyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione	——	C22H20N2O2	344.413
  ——	2-(2-dimethylaminoethyl)-5-(3-trifluormethylphenyl)benzo[de]isoquinoline-1,3-dione	——	C23H19F3N2O2	412.411
  ——	2-(2-dimethylaminoethyl)-5-(4-methoxyphenyl)benzo[de]isoquinoline-1,3-dione	——	C23H22N2O3	374.439
  ——	2-(2-dimethylaminoethyl)-5-(3-hydroxyphenyl)benzo[de]isoquinoline-1,3-dione	——	C22H20N2O3	360.412
  ——	2-(2-dimethylaminoethyl)-5-(3-methoxyphenyl)benzo[de]isoquinoline-1,3-dione	——	C23H22N2O3	374.439
  ——	2-(2-dimethylaminoethyl)-5-(2-methoxyphenyl)benzo[de]isoquinoline-1,3-dione	——	C23H22N2O3	374.439
  ——	5-(3'-nitro-phenyl)-2-[2-(dimethylamino)ethyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione	1098129-38-4	C22H19N3O4	389.411

反应信息

• 作为反应物：
  描述：

  2-(2-dimethylaminoethyl)-5-iodobenzo[de]isoquinoline-1,3-dione 、 3-硝基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 、 双氧水 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 13.0h， 以57%的产率得到5-(3'-nitro-phenyl)-2-[2-(dimethylamino)ethyl]-1H-benzo[de]isoquinoline-1,3(2H)-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 硫酸 、 sodium nitrite 、 potassium iodide 作用下， 以 水 、 丙酮 为溶剂， 反应 1.75h， 以44%的产率得到2-(2-dimethylaminoethyl)-5-iodobenzo[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

文献信息

• 5-Ethynylarylnaphthalimides as antitumor agents: Synthesis and biological evaluation
  作者：Patricia Quintana-Espinoza、Pedro Martín-Acosta、Ángel Amesty、Patricia Martín-Rodríguez、Isabel Lorenzo-Castrillejo、Leandro Fernández-Pérez、Félix Machín、Ana Estévez-Braun

  DOI：10.1016/j.bmc.2017.02.024

  日期：2017.3

  A set of 5-ethynylarylnaphthalimides was synthesized by Sonogashira cross-coupling reactions and evaluated for antiproliferative and antitopoisomerase II in vitro activities. Furthermore docking studies of these molecules as DNA-intercalators were carried out and the in vivo DNA-damaging activity was also determined with the model organism Saccharomyces cerevisiae. From the obtained results three naphthalimides

  通过Sonogashira交叉偶联反应合成了一组5-乙炔基芳基萘二甲酰亚胺，并评估了其在体外的抗增殖和抗拓扑异构酶II活性。此外，还对这些分子作为DNA嵌入剂进行了对接研究，并且还使用模型生物酿酒酵母（Saccharomyces cerevisiae）确定了体内的DNA破坏活性。从获得的结果来看，三种萘二甲酰亚胺6、13和14显示出强的拓扑异构酶II抑制活性。这三种分子也使用自互补寡聚脱氧核苷酸d（ATGCAT）2作为模型，作为DNA嵌入剂也表现出良好的对接分数，化合物13和14在体内DNA破坏活性中是最具细胞毒性的。