4-[(5,6-dicyano-3-diethylaminopyrazin-2-yl)methylamino]benzoic acid | 1203577-11-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-[(5,6-dicyano-3-diethylaminopyrazin-2-yl)methylamino]benzoic acid
• CAS: 1203577-11-0
• 化学式: C₁₈H₁₈N₆O₂
• 分子量: 350.38
• InChiKey: LFTMKBGKERMOET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  117.14
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-[(5,6-dicyano-3-diethylaminopyrazin-2-yl)methylamino]benzoic acid 、 5,6-bis(diethylamino)pyrazine-2,3-dicarbonitrile 在 lithium 作用下， 以 正丁醇 为溶剂， 反应 3.0h， 以15%的产率得到2-[(4-carboxyphenyl)methylamino]-3,9,10,16,17,23,24-heptakis(diethylamino)-1,4,11,15,18,22,25-(octaaza)phthalocyanine
  参考文献：
  名称：

  Solid-Phase Synthesis of Azaphthalocyanine−Oligonucleotide Conjugates and Their Evaluation As New Dark Quenchers of Fluorescence

  摘要：

  Hydrophobic nonaggregating metal-free azaphthalocyanines (AzaPc) of the tetrapyrazinoporphyrazine type were synthesized, characterized, and used for oligonucleotide labeling. Both 3'-end and 5'-end labeling methods using solid phase synthesis suitable for automatic processes in the DNA/RNA synthesizer were developed. The hydrophobic character of AzaPc enabled the anchoring of the conjugates on reverse phase of the oligonucleotide purification cartridge, thus enabling their simple purification. AzaPc did not show any fluorescence and extremely low singlet oxygen quantum yields (Phi(Delta) = 0.015-0.018 in DMF) in a monomeric state due to ultrafast intramolecular charge transfer. That is why they were investigated as a new dark quencher structural type. They profit particularly from absorption in a wide range of wavelengths (300-740 nm) that covers all fluorophores used in hybridization assays nowadays. As an example, quenching efficiency was evaluated in a simple hybridization assay using monolabeled probes. AzaPc-based probes efficiently quenched both fluorescein and Cy5 fluorescence by both resonance energy transfer and contact quenching. The results were compared with three established dark quenchers, and the AzaPc exerted better (BHQ-1 and BHQ-2) or comparable (BBQ-650) quenching efficiencies for both fluorophores.

  DOI：

  10.1021/bc100226x
• 作为产物：
  描述：

  4-甲氨基苯甲酸 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 4-[(5,6-dicyano-3-diethylaminopyrazin-2-yl)methylamino]benzoic acid
  参考文献：
  名称：

  Solid-Phase Synthesis of Azaphthalocyanine−Oligonucleotide Conjugates and Their Evaluation As New Dark Quenchers of Fluorescence

  摘要：

  Hydrophobic nonaggregating metal-free azaphthalocyanines (AzaPc) of the tetrapyrazinoporphyrazine type were synthesized, characterized, and used for oligonucleotide labeling. Both 3'-end and 5'-end labeling methods using solid phase synthesis suitable for automatic processes in the DNA/RNA synthesizer were developed. The hydrophobic character of AzaPc enabled the anchoring of the conjugates on reverse phase of the oligonucleotide purification cartridge, thus enabling their simple purification. AzaPc did not show any fluorescence and extremely low singlet oxygen quantum yields (Phi(Delta) = 0.015-0.018 in DMF) in a monomeric state due to ultrafast intramolecular charge transfer. That is why they were investigated as a new dark quencher structural type. They profit particularly from absorption in a wide range of wavelengths (300-740 nm) that covers all fluorophores used in hybridization assays nowadays. As an example, quenching efficiency was evaluated in a simple hybridization assay using monolabeled probes. AzaPc-based probes efficiently quenched both fluorescein and Cy5 fluorescence by both resonance energy transfer and contact quenching. The results were compared with three established dark quenchers, and the AzaPc exerted better (BHQ-1 and BHQ-2) or comparable (BBQ-650) quenching efficiencies for both fluorophores.

  DOI：

  10.1021/bc100226x

文献信息

• Effect of intramolecular charge transfer on fluorescence and singlet oxygen production of phthalocyanine analogues
  作者：Lenka Vachova、Veronika Novakova、Kamil Kopecky、Miroslav Miletin、Petr Zimcik

  DOI：10.1039/c2dt31403g

  日期：——

  decrease of fluorescence and singlet oxygen quantum yields. Photophysical and photochemical properties were compared to corresponding macrocycles that do not bear any donor centers. The data showed high feasibility of ICT in the tetrapyrazinoporphyrazine macrocycle and significantly lower efficiency of this deactivation process in the tribenzopyrazinoporphyrazine type molecules. Considerable effect of non-donor

  分子内电荷转移（ICT）进行了研究一系列镁，不含金属的和不对称tetrapyrazinoporphyrazines和tribenzopyrazinoporphyrazines带有两个二烷基氨基取代基（供体）和六烷基硫烷基或芳氧基取代基（非供体）的锌络合物。二烷基氨基取代基是导致ICT失活激发态并导致荧光和单线态氧量子产率显着下降的原因。将光物理和光化学性质与不带有任何供体中心的相应大环化合物进行了比较。数据表明，ICT在四吡嗪并卟啉大分子化合物中的可行性很高，而在三苯并吡嗪并卟啉类分子中这种失活过程的效率则大大降低。还描述了非供体外围取代基对ICT的显着影响。结果表明，四吡嗪并卟啉可能更适合开发基于ICT的应用中研究的新分子。