2-(2-((2-aminoethyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 906627-17-6

• 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-((2-aminoethyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 2-[2-(2-Aminoethylamino)ethyl]benzo[de]isoquinoline-1,3-dione
• CAS: 906627-17-6
• 化学式: C₁₆H₁₇N₃O₂
• 分子量: 283.33
• InChiKey: ANGCNBOMXAMPKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二茂铁甲醛 、 2-(2-((2-aminoethyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 以 甲醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  二茂铁附加的萘二甲酰亚胺衍生物：合成，DNA结合和体外细胞毒活性

  摘要：

  合成了三种新型的二茂铁附加的萘二甲酰亚胺衍生物（2a，2b和6），并通过IR，1 H NMR和质谱进行了表征。在电化学实验中，所有二茂铁附加的萘二甲酰亚胺衍生物在CV曲线中均表现出可逆的单电子氧化。并通过溴化乙锭置换实验和紫外可见分光光度法研究了这些化合物的DNA结合能力。在所有测试的化合物中，二茂铁附加的萘二甲酰亚胺衍生物6也表现出最高的DNA结合能力。根据粘度结果，所有合成的化合物均显示出与DNA双链体的部分嵌入结合模式。双萘二甲酰亚胺化合物使用5作为参考化合物，评价二茂铁附加的萘二甲酰亚胺衍生物6中二茂铁基团的协同作用。通过MTT分析研究了合成的化合物对4种不同的人类癌细胞系（EC109，BGC823，SGC 7901和HepG2）的细胞毒性。在所有合成的萘二甲酰亚胺衍生物和对照药物阿莫那肽中，二茂铁附加的双萘二甲酰亚胺衍生物6对测试的人类癌细胞显示出最佳的细胞毒性。通过激光共聚焦图

  DOI：

  10.1016/j.jorganchem.2019.03.001
• 作为产物：
  描述：

  1,8-萘二甲酸酐 、 二乙烯三胺 以 乙醇 为溶剂， 反应 4.0h， 生成 2-(2-((2-aminoethyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Exploring unsymmetrical dyads as efficient inhibitors against the insect β-N-acetyl-d-hexosaminidase OfHex2

  摘要：

  The GH20 beta-N-acetyl-D-hexosaminidase OfHex2 from the insect Ostrinia furnacalis (Guenee) is a target potential for eco-friendly pesticide development. Although carbohydrate-based inhibitors against beta-Nacetyl-D-hexosaminidases are widely studied, highly efficient, non-carbohydrate inhibitors are more attractive due to low cost and readily synthetic manner. Based on molecular modeling analysis of the catalytic domain of OfHex2, a series of novel naphthalimide-scaffold conjugated with a small aromatic moiety by an alkylamine spacer linker were designed and evaluated as efficiently competitive inhibitors against OfHex2. The most potent one containing naphthalimide and phenyl groups spanning by an N-alkylamine linker has a K-i value of 0.37 mu M, which is 6 fold lower than that of M-31850, the most potent non-carbohydrate inhibitor ever reported. The straightforward synthetic manners as well as the presumed binding model in this paper could be advantageous for further structural optimization for developing inhibitors against GH20 beta-N-acetyl-D-hexosaminidases. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2013.10.008

文献信息

• Ferrocene appended naphthalimide derivatives: Synthesis, DNA binding, and in vitro cytotoxic activity
  作者：Deng-Guo Jia、Jia-An Zheng、Yan-Ru Fan、Jian-Qiang Yu、Xiu-Li Wu、Bo-Jin Wang、Xin-Bin Yang、Yu Huang

  DOI：10.1016/j.jorganchem.2019.03.001

  日期：2019.6

  spectrophotometry. The ferrocene appended naphthalimide derivative 6 also exhibited the highest DNA binding ability in all the tested compounds. According to the viscosity results, all of the synthesized compounds displayed the partial intercalation binding mode to DNA duplex. Bis-naphthalimide compound 5 was used as reference compound to evaluate the synergistic effect of the ferrocene group in ferrocene appended

  合成了三种新型的二茂铁附加的萘二甲酰亚胺衍生物（2a，2b和6），并通过IR，1 H NMR和质谱进行了表征。在电化学实验中，所有二茂铁附加的萘二甲酰亚胺衍生物在CV曲线中均表现出可逆的单电子氧化。并通过溴化乙锭置换实验和紫外可见分光光度法研究了这些化合物的DNA结合能力。在所有测试的化合物中，二茂铁附加的萘二甲酰亚胺衍生物6也表现出最高的DNA结合能力。根据粘度结果，所有合成的化合物均显示出与DNA双链体的部分嵌入结合模式。双萘二甲酰亚胺化合物使用5作为参考化合物，评价二茂铁附加的萘二甲酰亚胺衍生物6中二茂铁基团的协同作用。通过MTT分析研究了合成的化合物对4种不同的人类癌细胞系（EC109，BGC823，SGC 7901和HepG2）的细胞毒性。在所有合成的萘二甲酰亚胺衍生物和对照药物阿莫那肽中，二茂铁附加的双萘二甲酰亚胺衍生物6对测试的人类癌细胞显示出最佳的细胞毒性。通过激光共聚焦图
• Exploring unsymmetrical dyads as efficient inhibitors against the insect β-N-acetyl-d-hexosaminidase OfHex2
  作者：Qi Chen、Peng Guo、Lin Xu、Tian Liu、Xuhong Qian、Qing Yang

  DOI：10.1016/j.biochi.2013.10.008

  日期：2014.2

  The GH20 beta-N-acetyl-D-hexosaminidase OfHex2 from the insect Ostrinia furnacalis (Guenee) is a target potential for eco-friendly pesticide development. Although carbohydrate-based inhibitors against beta-Nacetyl-D-hexosaminidases are widely studied, highly efficient, non-carbohydrate inhibitors are more attractive due to low cost and readily synthetic manner. Based on molecular modeling analysis of the catalytic domain of OfHex2, a series of novel naphthalimide-scaffold conjugated with a small aromatic moiety by an alkylamine spacer linker were designed and evaluated as efficiently competitive inhibitors against OfHex2. The most potent one containing naphthalimide and phenyl groups spanning by an N-alkylamine linker has a K-i value of 0.37 mu M, which is 6 fold lower than that of M-31850, the most potent non-carbohydrate inhibitor ever reported. The straightforward synthetic manners as well as the presumed binding model in this paper could be advantageous for further structural optimization for developing inhibitors against GH20 beta-N-acetyl-D-hexosaminidases. (C) 2013 Elsevier Masson SAS. All rights reserved.