N,N'-bis[3-(3-tert-butoxycarbonylaminopropyl)-methylaminopropyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide | 396718-27-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N'-bis[3-(3-tert-butoxycarbonylaminopropyl)-methylaminopropyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide
• 英文别名: tert-butyl N-[3-[methyl-[3-[13-[3-[methyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]propyl]-5,7,12,14-tetraoxo-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaen-6-yl]propyl]amino]propyl]carbamate
• CAS: 396718-27-7
• 化学式: C₃₈H₅₄N₆O₈
• 分子量: 722.882
• InChiKey: HPARZXKGNJQZQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  52.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  157.9
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N,N'-bis[3-(3-tert-butoxycarbonylaminopropyl)-methylaminopropyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 生成
  参考文献：
  名称：

  具有增强的稳定二聚体G-四链体能力的环状萘二酰亚胺二聚体

  摘要：

  设计并合成了一种新型的带有变化的接头长度的二聚环萘二酰亚胺衍生物（cNDI-二聚体），以识别二聚体G-四链体结构。所有cNDI-二聚体均表现出较高的识别G-四链体结构的偏好，并且通过将熔融温度提高23°C以上而显着增强了二聚G-四链体结构相对于cNDI单体的热稳定性。 cNDI二聚体稳定二聚体G-四链体的能力。cNDI二聚体还显示出比cNDI单体更强的抑制端粒酶活性和阻止端粒DNA延伸的能力，这显示出更高的抗癌潜力，可用于进一步的治疗应用。

  DOI：

  10.1002/chem.201901468
• 作为产物：
  描述：

  S-Boc-2-巯基-4,6-二甲基嘧啶 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 N,N'-bis[3-(3-tert-butoxycarbonylaminopropyl)-methylaminopropyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide
  参考文献：
  名称：

  Ferrocenyl naphthalene diimide can bind to DNA·RNA hetero duplex: potential use in an electrochemical detection of mRNA expression

  摘要：

  The novel ferrocenyl naphthalene diimide derivative I was synthesized by the condensation reaction between ferroceneacetic acid and terminal amino moieties of two imide substituents of naphthalene diimide. Stopped-flow analysis of the ligand I and DNA interaction revealed the following results: (i) the ligand binds to double stranded DNA more strongly than to single stranded DNA; (ii) the ligand does not have a bias against DNA sequence; (iii) the ligand can bind to the DNA-RNA hetero duplex more strongly than to the DNA-DNA duplex. These properties of I make it a suitable ligand for analysis of not only DNA but RNA. In fact, a current due to I was observed at 269 mV in the differential pulse voltammetric analysis of dA(20)-immobilized electrode in an electrolyte containing 1. The current increased markedly upon hybridization with polyU, whereas no current increase was obtained for polyA. Since the DNA-RNA hetero duplex is formed between sample RNA and DNA on the electrode, I may be used for the electrochemical detection of mRNA expression. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00951-2

文献信息

• Self-stacking of naphthalene bis(dicarboximide)s probed by NMR †
  作者：Vera Steullet、Dabney W. Dixon

  DOI：10.1039/a801441h

  日期：——

  The self-stacking in water of a series of naphthalene-1,8∶4,5-bis(dicarboximide)s (also known as naphthalene diimides, NDIs) bearing cationic side chains has been studied using NMR techniques. The position of the charge in the side chain has a strong effect on the propensity of the NDI to self-stack. Examples with a cationic center three atoms away from the NDI ring in general do not self-stack; those with cationic centers further out on the side chains are prone to self-stack at NMR concentrations. The size of the side chain per se does not appear to be a significant controlling factor; even a derivative with biotin side chains shows no evidence of self-stacking. Increasing the ionic strength of the solution can also induce stacking. Derivatives with aromatic side chains can show intramolecular self-stacking of the side chain with the central NDI ring. This is significant for side chains with isoquinoline and bipyridine groups but not significant for side chains with pyridine groups. An example of an NDI that undergoes both intramolecular and intermolecular stacking is the derivative bearing side chains ending in Ru(bpy)32+ moieties. In methanol, the shift patterns of the aromatic resonances of the bipyridine rings are very close to those of a model compound. However, a more complicated chemical shift pattern is seen in water. This indicates that conformations with the Ru(bpy)32+ moieties lying at least partly within the shielding cone of the aromatic NDI system are favored. Molecular modeling indicates that conformations in which the bipyridine ring interacts with the NDI ring are readily achievable. The temperature dependence of the chemical shifts for this molecule indicates that both intramolecular interactions of the bipyridine rings with the NDI ring and self-stacking of the NDI rings are significant.

  使用核磁共振技术研究了一系列带有阳离子侧链的萘-1,8‖4,5-双(二氧亚胺)(也称为萘二亚胺,NDI)在水中的自堆叠现象。侧链上的电荷位置对NDI的自堆叠倾向有强烈影响。通常,阳离子中心与NDI环相隔三原子的例子不会自堆叠;而阳离子中心位于侧链更远处的则倾向于在核磁共振浓度下自堆叠。侧链的大小本身似乎不是重要的控制因素;甚至带有生物素侧链的衍生物也未显示出自堆叠的证据。增加溶液的离子强度也可以诱导堆叠。带有芳香侧链的衍生物可以显示侧链与中央NDI环的分子内自堆叠。这对于带有异喹啉和联吡啶基团的侧链是显著的,但对于带有吡啶基团的侧链则不显著。一个同时经历分子内和分子间堆叠的NDI例子是带有侧链末端为Ru(bpy)32+基团的衍生物。在甲醇中,联吡啶环的芳香共振位移模式与模型化合物非常接近。然而,在水中的化学位移模式更为复杂。这表明,Ru(bpy)32+基团至少部分位于芳香NDI系统的屏蔽锥内的构象是受青睐的。分子模拟表明,联吡啶环与NDI环相互作用的构象容易实现。该分子化学位移的温度依赖性表明,联吡啶环与NDI环的分子内相互作用以及NDI环的自堆叠都是显著的。
• Cyclic ferrocenylnaphthalene diimides as a probe for electrochemical telomerase assay
  作者：Shuma Kaneyoshi、Nao Eguchi、Kazuhisa Fujimoto、Satoshi Fujii、Shinobu Sato、Shigeori Takenaka

  DOI：10.1016/j.jinorgbio.2022.111746

  日期：2022.5