2-(2-(dimethylamino)ethyl)-6-((2-hydroxyethyl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1357258-26-4

• 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-(dimethylamino)ethyl)-6-((2-hydroxyethyl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 2-[2-(Dimethylamino)ethyl]-6-(2-hydroxyethylamino)benzo[de]isoquinoline-1,3-dione
• CAS: 1357258-26-4
• 化学式: C₁₈H₂₁N₃O₃
• 分子量: 327.383
• InChiKey: NXESMBZHQNZOSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 以 2-methoxymethanol 、 乙醇 为溶剂， 反应 7.0h， 生成 2-(2-(dimethylamino)ethyl)-6-((2-hydroxyethyl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  DNA binding and anticancer activity of naphthalimides with 4-hydroxyl-alkylamine side chains at different lengths

  摘要：

  A series of novel naphthalimide derivatives modified with various hydroxyl-alkylamines at 4-position have been synthesized. Their DNA binding properties were investigated by UV-Vis, fluoescence, and circular dichroism (CD) spectroscopies and thermal denaturation. The results showed that compounds 3a-e as the DNA intercalator exhibited middle binding affinities with Ct-DNA. The anticancer activities of 3a-e were preliminarily evaluated, compounds 3c and 3e exhibited potent anticancer activities against Bel-7402 cell line with IC50 values of 5.57 and 9.17 mu M, respectively. More interestingly, enhancement of the fluorescence emission was found in the complexes of 3a-e with Ct-DNA, especially for 3c. This would make these compounds as potential DNA staining agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.018

文献信息

• Naphthalimide-based macrophage nucleus imaging probes
  作者：Francisco Fueyo-González、Mar Fernández-Gutiérrez、Diego García-Puentes、Angel Orte、Juan A. González-Vera、Rosario Herranz

  DOI：10.1016/j.ejmech.2020.112407

  日期：2020.8

  can be easily tuned by chemical manipulation of the substituents on that privileged scaffold. Replacement of a OMe group at position 6 in 2-(hydroxyl)ethyl-naphthalimide derivatives by diverse amines, including 2-(hydroxyl)ethylamine, trans-(4-acetamido)cyclohexylamine and azetidine increases the solvatochromic (ICT) character, while this replacement in 2-(dimethylamino)ethyl-naphthalimide analogues

  基于萘二甲酰亚胺的荧光团的光物理性质可以通过对该特权支架上的取代基进行化学处理而容易地调节。2-（羟基）乙基-萘二甲酰亚胺衍生物中第6位的OMe基被包括2-（羟基）乙胺，反式-（4-乙酰氨基）环己胺和氮杂环丁烷在内的多种胺取代，增加了溶剂致变色（ICT）特性，而这替换为2-（二甲基氨基）乙基-萘二甲酰亚胺类似物（PET荧光团）会降低其溶剂极性敏感性，甚至将其反转为溶剂变色荧光团。这些荧光团产生了巨噬细胞核成像探针，该探针结合DNA作为嵌入剂，并在人类癌细胞中显示出低细胞毒性。
• DNA binding and anticancer activity of naphthalimides with 4-hydroxyl-alkylamine side chains at different lengths
  作者：Kerang Wang、Yueqing Wang、Xinhao Yan、Hua Chen、Gang Ma、Pingzhu Zhang、Jinmei Li、Xiaoliu Li、Jinchao Zhang

  DOI：10.1016/j.bmcl.2011.12.018

  日期：2012.1

  A series of novel naphthalimide derivatives modified with various hydroxyl-alkylamines at 4-position have been synthesized. Their DNA binding properties were investigated by UV-Vis, fluoescence, and circular dichroism (CD) spectroscopies and thermal denaturation. The results showed that compounds 3a-e as the DNA intercalator exhibited middle binding affinities with Ct-DNA. The anticancer activities of 3a-e were preliminarily evaluated, compounds 3c and 3e exhibited potent anticancer activities against Bel-7402 cell line with IC50 values of 5.57 and 9.17 mu M, respectively. More interestingly, enhancement of the fluorescence emission was found in the complexes of 3a-e with Ct-DNA, especially for 3c. This would make these compounds as potential DNA staining agents. (C) 2011 Elsevier Ltd. All rights reserved.