(2-(N-pyridinium)-ethyl)-4-amino-1,8-naphthalimide | 1372860-95-1

• 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-(N-pyridinium)-ethyl)-4-amino-1,8-naphthalimide
• 英文别名: 6-Amino-2-(2-pyridin-1-ium-1-ylethyl)benzo[de]isoquinoline-1,3-dione;chloride
• CAS: 1372860-95-1
• 化学式: C₁₉H₁₆N₃O₂*Cl
• 分子量: 353.808
• InChiKey: JPNBWLNOXYXJAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.99
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-(N-pyridinium)-ethyl)-4-amino-1,8-naphthalimide 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 bis[[2-(N-pyridinium)ethyl]]-9,18-methano-1,8-naphthalimido[b,f ][1,5]diazocine dichloride
  参考文献：
  名称：

  Supramolecular Approach to Enantioselective DNA Recognition Using Enantiomerically Resolved Cationic 4-Amino-1,8-naphthalimide-Based Tröger’s Bases

  摘要：

  The synthesis and photophysical studies of two cationic base (TB)-derived bis-naphthalimides 1 and 2 and the TB derivative 6, characterized by X-ray crystallography, are presented. The enantiomers of 1 and 2 are separated by cation-exchange chromatography on Sephadex C25 using sodium (-)-dibenzoyl-l-tartarate as the chiral mobile phase. The binding of enantiomers with salmon testes (st)-DNA and synthetic polynucleotides are studied by a variety of spectroscopic methods including UV/vis absorbance, circular dichroism, linear dichroism, and ethidium bromide displacement assays, which demonstrated binding of these compounds to the DNA grooves with very high affinity (K similar to 10(6) M-1) and preferential binding of (-)-enantiomer. In all cases, binding to DNA resulted in a significant stabilization of the double-helical structure of DNA against thermal denaturation. Compound (+/-)-2 and its enantiomers possessed significantly higher binding affinity for double-stranded DNA compared to 1, possibly due to the presence of the methyl group, which allows favorable hydrophobic and van der Waals interactions with DNA. The TB derivatives exhibited marked preference for AT rich sequences, where the binding affinities follow the order (-)-enantiomer > (+/-) > (+)-enantiomer. The compounds exhibited significant photocleavage of plasmid DNA upon visible light irradiation and are rapidly internalized into malignant cell lines.

  DOI：

  10.1021/jo501711g
• 作为产物：
  描述：

  6-Amino-2-(2-pyridin-1-ium-1-ylethyl)benzo[de]isoquinoline-1,3-dione;hexafluorophosphate 在 DOWEX-1x8-200 Cl(-) 作用下， 以 甲醇 为溶剂， 以0.6 g的产率得到(2-(N-pyridinium)-ethyl)-4-amino-1,8-naphthalimide
  参考文献：
  名称：

  吡啶鎓4-氨基-1,8-萘二甲酰亚胺衍生物的合成和光物理评估，该衍生物在插入后显示出对富含AT的双链DNA的偏好†

  摘要：

  描述了阳离子4-氨基-1,8-萘二甲酰亚胺衍生物（1）的合成，表征和固态晶体结构。显示1的光物理性质随溶剂极性和H键合能力而变化。1的荧光在其与5'-腺苷-单磷酸的1：1复合物中被增强和蓝移，而在其与5'-鸟苷-单磷酸的复合物中被部分淬灭和红移。线性和圆形二向色性测量结果表明1通过插入与双链DNA结合。使用双链合成多核苷酸poly（dA–dT）2和poly（dG–dC）2进行的紫外可见和荧光比较研究表明，1与AT聚合物更牢固地结合；1还强烈倾向于天然DNA中富含A–T的序列。热变性测量还显示，双链poly（dA–dT）2的稳定性比天然DNA强得多。

  DOI：

  10.1039/c2ob06898b

文献信息

• Synthesis and photophysical evaluation of a pyridinium 4-amino-1,8-naphthalimide derivative that upon intercalation displays preference for AT-rich double-stranded DNA
  作者：Swagata Banerjee、Jonathan A. Kitchen、Thorfinnur Gunnlaugsson、John M. Kelly

  DOI：10.1039/c2ob06898b

  日期：——

  The synthesis, characterisation and solid state crystal structure of a cationic 4-amino-1,8-naphthalimide derivative (1) are described. The photophysical properties of 1 are shown to vary with the solvent polarity and H-bonding ability. The fluorescence of 1 is enhanced and blue-shifted in its 1 : 1 complex with 5′-adenosine-monophosphate while it is partially quenched and red-shifted in its complex

  描述了阳离子4-氨基-1,8-萘二甲酰亚胺衍生物（1）的合成，表征和固态晶体结构。显示1的光物理性质随溶剂极性和H键合能力而变化。1的荧光在其与5'-腺苷-单磷酸的1：1复合物中被增强和蓝移，而在其与5'-鸟苷-单磷酸的复合物中被部分淬灭和红移。线性和圆形二向色性测量结果表明1通过插入与双链DNA结合。使用双链合成多核苷酸poly（dA–dT）2和poly（dG–dC）2进行的紫外可见和荧光比较研究表明，1与AT聚合物更牢固地结合；1还强烈倾向于天然DNA中富含A–T的序列。热变性测量还显示，双链poly（dA–dT）2的稳定性比天然DNA强得多。
• Supramolecular Approach to Enantioselective DNA Recognition Using Enantiomerically Resolved Cationic 4-Amino-1,8-naphthalimide-Based Tröger’s Bases
  作者：Swagata Banerjee、Sandra A. Bright、Jayden A. Smith、Jeremy Burgeat、Miguel Martinez-Calvo、D. Clive Williams、John M. Kelly、Thorfinnur Gunnlaugsson

  DOI：10.1021/jo501711g

  日期：2014.10.3

  The synthesis and photophysical studies of two cationic base (TB)-derived bis-naphthalimides 1 and 2 and the TB derivative 6, characterized by X-ray crystallography, are presented. The enantiomers of 1 and 2 are separated by cation-exchange chromatography on Sephadex C25 using sodium (-)-dibenzoyl-l-tartarate as the chiral mobile phase. The binding of enantiomers with salmon testes (st)-DNA and synthetic polynucleotides are studied by a variety of spectroscopic methods including UV/vis absorbance, circular dichroism, linear dichroism, and ethidium bromide displacement assays, which demonstrated binding of these compounds to the DNA grooves with very high affinity (K similar to 10(6) M-1) and preferential binding of (-)-enantiomer. In all cases, binding to DNA resulted in a significant stabilization of the double-helical structure of DNA against thermal denaturation. Compound (+/-)-2 and its enantiomers possessed significantly higher binding affinity for double-stranded DNA compared to 1, possibly due to the presence of the methyl group, which allows favorable hydrophobic and van der Waals interactions with DNA. The TB derivatives exhibited marked preference for AT rich sequences, where the binding affinities follow the order (-)-enantiomer > (+/-) > (+)-enantiomer. The compounds exhibited significant photocleavage of plasmid DNA upon visible light irradiation and are rapidly internalized into malignant cell lines.