2,7-bis(5-aminopentyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone | 1191058-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,7-bis(5-aminopentyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
• 英文别名: 6,13-Bis(5-aminopentyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• CAS: 1191058-98-6
• 化学式: C₂₄H₂₈N₄O₄
• 分子量: 436.511
• InChiKey: PETPSYQBUDGUJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,7-bis(5-aminopentyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone 、 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：

  1,5-二氨基戊烷 、 1,4,5,8-萘四甲酸酐 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 生成 2,7-bis(5-aminopentyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
  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.