2-Amino-6-dimethylamino-benzo[e]perimidin-7-one | 438201-53-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-Amino-6-dimethylamino-benzo[e]perimidin-7-one
• 英文别名: 2-Amino-6-(dimethylamino)benzo[e]perimidin-7-one
• CAS: 438201-53-7
• 化学式: C₁₇H₁₄N₄O
• 分子量: 290.324
• InChiKey: NKYIFBKLQWBNKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Amino-6-dimethylamino-benzo[e]perimidin-7-one 在 四甲基乙二胺 、 sodium amide 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 2,6-di[[(2-dimethylamino)ethyl]amino]-7H-benzo[e]perimidin-7-one
  参考文献：
  名称：

  Effect of Modification of 6-[(Aminoalkyl)amino]-7H-benzo[e]-perimidin-7-ones on Their Cytotoxic Activity Toward Sensitive and Multidrug Resistant Tumor Cell Lines. Synthesis and Biological Evaluation

  摘要：

  Benzoperimidines, a novel group of antitumor anthracenedione analogues, are of interest due to their ability to overcome multidrug resistance of tumor cells (Stefanska, B., Dzieduszycka, M., Bontemps-Gracz, M. M., Borowski, E., Martelli, S., Supino, R., Pratesi, G., De Cesare, MA., Zunino, F., Kusnierczyk, H., Radzikowski, Cz. J. Med. Chem. 1999, 42, 3494). Although the structural factor essential for exhibiting this desirable property is the presence in the molecule of a fused heterocyclic ring, the cytotoxicity against resistant cells is highly influenced by the nature and location of the substituents. A series of novel synthetic derivatives, comprising monohydroxylated benzoperimidines and 2-aminobenzoperimidines, allowed the establishment of an in vitro structure-activity relationship for a panel of leukemia sensitive, as well as P-gp dependent multidrug resistance (MDR) and multidrug resistance associated protein dependent resistance (MRP) resistant cell lines. The membrane affinity for the compounds has also been determined. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00358-3
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 盐酸胍 、 1,4-二氯蒽醌 在 sodium hydroxide 、 铜 作用下， 反应 4.0h， 以40%的产率得到2-Amino-6-dimethylamino-benzo[e]perimidin-7-one
  参考文献：
  名称：

  Effect of Modification of 6-[(Aminoalkyl)amino]-7H-benzo[e]-perimidin-7-ones on Their Cytotoxic Activity Toward Sensitive and Multidrug Resistant Tumor Cell Lines. Synthesis and Biological Evaluation

  摘要：

  Benzoperimidines, a novel group of antitumor anthracenedione analogues, are of interest due to their ability to overcome multidrug resistance of tumor cells (Stefanska, B., Dzieduszycka, M., Bontemps-Gracz, M. M., Borowski, E., Martelli, S., Supino, R., Pratesi, G., De Cesare, MA., Zunino, F., Kusnierczyk, H., Radzikowski, Cz. J. Med. Chem. 1999, 42, 3494). Although the structural factor essential for exhibiting this desirable property is the presence in the molecule of a fused heterocyclic ring, the cytotoxicity against resistant cells is highly influenced by the nature and location of the substituents. A series of novel synthetic derivatives, comprising monohydroxylated benzoperimidines and 2-aminobenzoperimidines, allowed the establishment of an in vitro structure-activity relationship for a panel of leukemia sensitive, as well as P-gp dependent multidrug resistance (MDR) and multidrug resistance associated protein dependent resistance (MRP) resistant cell lines. The membrane affinity for the compounds has also been determined. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00358-3