2-(2-(dimethylamino)ethyl)-6-(2-(dimethylamino)ethylamino)-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione | 906716-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-(dimethylamino)ethyl)-6-(2-(dimethylamino)ethylamino)-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 2-[2-(Dimethylamino)ethyl]-6-[2-(dimethylamino)ethylamino]-5-nitrobenzo[de]isoquinoline-1,3-dione
• CAS: 906716-19-6
• 化学式: C₂₀H₂₅N₅O₄
• 分子量: 399.45
• InChiKey: ZKKCYAOLVJOZCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-(dimethylamino)ethyl)-6-(2-(dimethylamino)ethylamino)-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione 生成 2-[2-(dimethylamino)ethyl]-6-{[2-(dimethylamino)ethyl]-amino}-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione hydrochloride
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of new mitonafide derivatives as potential antitumor drugs

  摘要：

  A series of potential DNA-binding antitumor agents, 2-[omega-(alkylamino) alkyl]-6-{[omega-(alkylamino) alkyl] amino}-1H-benzo[de] isoquinolin-1,3(2H)-diones and 1,7-bis{6-[(omega-(dimethylamino) alkyl) amino]-1,3dioxo-1H-benzo[de] isoquinolin-2(3H)-yl}-4-methyl-4-azaheptanes, have been prepared as mitonafide derivatives. Their DNA-binding ability and cytotoxic activity have been evaluated. Some of the target compounds have shown high DNA affinity as well as relevant cytotoxic properties. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.027
• 作为产物：
  描述：

  3-nitro-4-chloro-1,8-naphthalene dicarboxylic acid anhydride 、 N,N-二甲基乙二胺 以 氯仿 为溶剂， 反应 3.0h， 以42%的产率得到2-(2-(dimethylamino)ethyl)-6-(2-(dimethylamino)ethylamino)-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of new mitonafide derivatives as potential antitumor drugs

  摘要：

  A series of potential DNA-binding antitumor agents, 2-[omega-(alkylamino) alkyl]-6-{[omega-(alkylamino) alkyl] amino}-1H-benzo[de] isoquinolin-1,3(2H)-diones and 1,7-bis{6-[(omega-(dimethylamino) alkyl) amino]-1,3dioxo-1H-benzo[de] isoquinolin-2(3H)-yl}-4-methyl-4-azaheptanes, have been prepared as mitonafide derivatives. Their DNA-binding ability and cytotoxic activity have been evaluated. Some of the target compounds have shown high DNA affinity as well as relevant cytotoxic properties. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.027

文献信息

• Derivatives of 5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione: design, synthesis, and biological activity
  作者：Aibin Wu、Jide Liu、Shaoxiong Qin、Ping Mei

  DOI：10.1007/s00706-009-0220-9

  日期：2010.1

  values of 10−6–10−5 M. More importantly, the derivatives had distinct antitumor selectivity against different cancer cell lines. This work provided a novel class of mitonafide-based lead compounds with improved antitumor selectivity against cancer cell lines for further optimization. Graphical Abstract

  摘要一系列具有不同氨基侧链的单和双-2-（2-（二甲基氨基）-乙基）-5-硝基-1 H-苯并[ de ]异喹啉-1,3（2 H）-二酮，一个新的家族已经设计并合成了抗肿瘤药。体外评估了它们对HeLa，A549，P388，HL-60，MCF-7，HCT-8和A375癌细胞系的抗肿瘤活性。初步结果表明，大多数衍生物的抗肿瘤活性与米托那肽相当，IC 50值为10 -6 –10 -5 M.更重要的是，这些衍生物对不同的癌细胞系具有独特的抗肿瘤选择性。这项工作提供了一类新型的基于mitonafide的先导化合物，具有针对癌细胞系的改进的抗肿瘤选择性，可进一步优化。 图形概要