2-(7-aminoheptyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1191059-04-7

• 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-(7-aminoheptyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 2-(7-Aminoheptyl)benzo[de]isoquinoline-1,3-dione
• CAS: 1191059-04-7
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: IXITYNIFNXDFPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(7-aminoheptyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 、 邻甲氧基苯甲醛 以 甲苯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Substituted Naphthalene Imides and Diimides as Anticancer Agent

  摘要：

  Naphthalimmide (NI) and 1,4,5,8-naphthalenetetracarboxylic diimide (NDI) derivatives were synthesized and evaluated for their antiproliferative activity. NDI derivatives 1-9 were more cytotoxic than the corresponding NI derivatives 10-18. The molecular mechanisms of 1 and 2 were investigated in comparison to mitonafide. They interacted with DNA, were not topoisomerase II alpha poisons, triggered caspase activation, caused p53 protein accumulation, and down-regulated AKT survival. Furthermore, 1 and 2 caused a decrease of ERK1/2 and, unlike mitonafide, inhibited ERKs phosphorylation.

  DOI：

  10.1021/jm901131m
• 作为产物：
  描述：

  1,8-萘二甲酸酐 、 1,7-二氨基庚烷 以 乙醇 为溶剂， 反应 24.0h， 以85%的产率得到2-(7-aminoheptyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Substituted Naphthalene Imides and Diimides as Anticancer Agent

  摘要：

  Naphthalimmide (NI) and 1,4,5,8-naphthalenetetracarboxylic diimide (NDI) derivatives were synthesized and evaluated for their antiproliferative activity. NDI derivatives 1-9 were more cytotoxic than the corresponding NI derivatives 10-18. The molecular mechanisms of 1 and 2 were investigated in comparison to mitonafide. They interacted with DNA, were not topoisomerase II alpha poisons, triggered caspase activation, caused p53 protein accumulation, and down-regulated AKT survival. Furthermore, 1 and 2 caused a decrease of ERK1/2 and, unlike mitonafide, inhibited ERKs phosphorylation.

  DOI：

  10.1021/jm901131m

文献信息

• Design, Synthesis, and Biological Evaluation of Substituted Naphthalene Imides and Diimides as Anticancer Agent
  作者：Vincenzo Tumiatti、Andrea Milelli、Anna Minarini、Marialuisa Micco、Anna Gasperi Campani、Laura Roncuzzi、Daniela Baiocchi、Jessica Marinello、Giovanni Capranico、Maddalena Zini、Claudio Stefanelli、Carlo Melchiorre

  DOI：10.1021/jm901131m

  日期：2009.12.10

  Naphthalimmide (NI) and 1,4,5,8-naphthalenetetracarboxylic diimide (NDI) derivatives were synthesized and evaluated for their antiproliferative activity. NDI derivatives 1-9 were more cytotoxic than the corresponding NI derivatives 10-18. The molecular mechanisms of 1 and 2 were investigated in comparison to mitonafide. They interacted with DNA, were not topoisomerase II alpha poisons, triggered caspase activation, caused p53 protein accumulation, and down-regulated AKT survival. Furthermore, 1 and 2 caused a decrease of ERK1/2 and, unlike mitonafide, inhibited ERKs phosphorylation.