N,N'-bis-(3-(4-morpholino)-propyl)-3,4,9,10-perylenetetracarboxylic acid diimide

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-bis-(3-(4-morpholino)-propyl)-3,4,9,10-perylenetetracarboxylic acid diimide
• 英文别名: N,N'-bis(3-morpholinopropyl)-3,4,9,10-perylenetetracarboxylic acid diimide；7,18-Bis(3-morpholin-4-ylpropyl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
• 化学式: C₃₈H₃₆N₄O₆
• 分子量: 644.727
• InChiKey: CULAZNNOUPDNAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  99.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-(3-氨丙基)吗啉 、 3,4,9,10-苝四羧酸二酐 以 正丁醇 为溶剂， 生成 N,N'-bis-(3-(4-morpholino)-propyl)-3,4,9,10-perylenetetracarboxylic acid diimide
  参考文献：
  名称：

  ylene二酰亚胺G-四链体DNA结合选择性是由配体聚集介导的。

  摘要：

  两个N，N'-二取代的ylene二酰亚胺G-四链体DNA配体，PIPER [N，N'-双-（2-（1-哌啶子基）乙基）-3,4,9,10-per四羧酸二酰亚胺]和Tel01研究了[N，N′-双-（3-（4-吗啉代）-丙基）-3,4,9,10-per四羧酸二酰亚胺]。可见吸收，共振光散射和荧光光谱用于表征这些配体的pH依赖性聚集。通过吸收光谱法监测的这些配体的G-四链体DNA结合选择性也是pH依赖性的。配体在低pH条件下结合双链体DNA和G-四链体DNA，此时配体不聚集。在较高的pH下，配体大量聚集，表观的G-四链体DNA结合选择性很高。

  DOI：

  10.1016/s0960-894x(01)00775-2

文献信息

• Perylene Diimide G-Quadruplex DNA Binding Selectivity is Mediated by Ligand Aggregation
  作者：Sean M. Kerwin、Grace Chen、Jonathan T. Kern、Pei Wang Thomas

  DOI：10.1016/s0960-894x(01)00775-2

  日期：2002.2

  N'-disubstituted perylene diimide G-quadruplex DNA ligands, PIPER [N,N'-bis-(2-(1-piperidino)ethyl)-3,4,9,10-perylene tetracarboxylic acid diimide] and Tel01 [N,N'-bis-(3-(4-morpholino)-propyl)-3,4,9,10-perylene tetracarboxylic acid diimide] were studied. Visible absorbance, resonance light scattering, and fluorescence spectroscopy were used to characterize the pH-dependent aggregation of these ligands. The G-quadruplex

  两个N，N'-二取代的ylene二酰亚胺G-四链体DNA配体，PIPER [N，N'-双-（2-（1-哌啶子基）乙基）-3,4,9,10-per四羧酸二酰亚胺]和Tel01研究了[N，N′-双-（3-（4-吗啉代）-丙基）-3,4,9,10-per四羧酸二酰亚胺]。可见吸收，共振光散射和荧光光谱用于表征这些配体的pH依赖性聚集。通过吸收光谱法监测的这些配体的G-四链体DNA结合选择性也是pH依赖性的。配体在低pH条件下结合双链体DNA和G-四链体DNA，此时配体不聚集。在较高的pH下，配体大量聚集，表观的G-四链体DNA结合选择性很高。
• Selective interactions of perylene derivatives having different side chains with inter- and intramolecular G-quadruplex DNA structures. A correlation with telomerase inhibition
  作者：Luigi Rossetti、Marco Franceschin、Stefano Schirripa、Armandodoriano Bianco、Giancarlo Ortaggi、Maria Savino

  DOI：10.1016/j.bmcl.2004.10.061

  日期：2005.1

  While the importance of the aromatic core in small organic molecules, studied as G-quadruplex mediated telomerase inhibitors, appears well studied by a number of researches, the role of side chains has been less well characterized. In this paper, we have studied the ability of six perylene derivatives with different side chains to induce both inter- and intramolecular G-quadruplex structures. The distance between the aromatic core and the positive charges in the side chains emerges as a significant molecular feature in G-quadruplex formation. Furthermore, the G-quadruplex formation appears also related to drugs 'self-association', influenced by the side chains basicity. The different efficiencies of the six perylene derivatives in interacting both with inter- and intramolecular G-quadruplex structures satisfactorily correlate with telomerase inhibition in cell-free systems. (C) 2004 Elsevier Ltd. All rights reserved.
• Near-infrared reflective properties of perylene derivatives
  作者：Balwinder Kaur、Nurul Quazi、Ivan Ivanov、S.N. Bhattacharya

  DOI：10.1016/j.dyepig.2011.06.011

  日期：2012.3

  Dyes and pigments with high reflectance in the near-infrared (NIR) region can extensively control the heat buildup. Perylene-based pigments exhibit considerable reflectance in the NIR region. The reflectance of a material depends upon a number of factors, such as particle size, concentration of the reflective material, the distribution of particles within the material and the material's refractive index. The refractive index, in turn, depends on the electronic structure of the material. Therefore,differently substituted perylene compounds are expected to exhibit different reflectance in the NIR region. To elaborate this point, different perylene bisimide derivatives have been synthesized, and their ability to reflect in the NIR region has been determined and compared to the results for commercially available pigments. Significant variation in the relative reflectance is observed in the NIR region for differently substituted perylene bisimide compounds. The NIR reflectance of different perylene tetracarboxy diimide derivatives (PCIs) was also compared to the reflectance of 3,4:9,10-perylenetetracarboxylic dianhydride (PTCA), the precursor from which the PCIs are commonly synthesized. PICA exhibits significantly higher relative reflectance in the given region than any of the diimide derivatives synthesized from it in this study. (C) 2011 Elsevier Ltd. All rights reserved.