4'-methyl-N-(naphthalene-2-yl)-2,2'-bipyridine-4-carboxyamide

• 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: 4'-methyl-N-(naphthalene-2-yl)-2,2'-bipyridine-4-carboxyamide
• 英文别名: 4'-methyl-N-(naphthalen-2-yl)-2,2'-bipyridine-4-carboxyamide；2-(4-methylpyridin-2-yl)-N-naphthalen-2-ylpyridine-4-carboxamide
• 化学式: C₂₂H₁₇N₃O
• 分子量: 339.396
• InChiKey: UHELQGJBAMEJLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 [Ru(bpy)(dppz)Cl₂] 、 4'-methyl-N-(naphthalene-2-yl)-2,2'-bipyridine-4-carboxyamide 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  芳基取代的钌（II）配合物：增强光裂解和有效的DNA结合的策略。

  摘要：

  钌多吡啶复合物已显示出有望用作光动力疗法（PDT）的试剂和分子生物学工具（生色团辅助的光灭活）。为了完成这些任务，重要的是至少要具有目标选择性和巨大的活性氧（ROS）光生能：在同一分子中不容易发现的两个特性。为了制备这种新试剂，我们合成了两种新的钌配合物，它们结合了有效的DNA结合部分（dppz配体）与萘基修饰的（1）和蒽基修饰的（2）联吡啶作为结合到钌配合物上的强ROS产生剂。对该化合物进行了充分表征，并研究了它们的光物理和光化学性质。化合物2表明曾报道为单线态氧产生的最高量子产率中的一个（Φ Δ = 0.96），具有非常高的DNA结合沿（日志ķ b= 6.78）。这种光化学行为可归因于较低的三重态，涉及蒽基修饰的联吡啶，这与较容易的氧猝灭有关。此外，这些化合物对G-四链体DNA表现出中等选择性，并与DNA的小沟结合，这很可能是由侧基配体驱动的。有趣的是，即使暴露于黄色发光二极管（LED

  DOI：

  10.1021/acs.inorgchem.7b01108
• 作为产物：
  描述：

  4'-甲基-2,2'-联吡啶-4-甲酸 、 2-萘胺 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 N-甲基吗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 以77%的产率得到4'-methyl-N-(naphthalene-2-yl)-2,2'-bipyridine-4-carboxyamide
  参考文献：
  名称：

  Ruthenium(II) bipyridine complexes with pendant anthracenyl and naphthyl moieties: A strategy for a ROS generator with DNA binding selectivity

  摘要：

  Coordination compounds that combine selective DNA binding with reactive oxygen species (ROS) generation production have been sought as tools for cell biology studies and cancer therapy. In this respect, the contribution of this work lies on the use of anthracenyl (Ru-Anth) and naphthalyl-pedant (Ru-Naph) ruthenium(II) bipyridine complexes, which were synthesized and fully characterized by spectroscopic and electrochemical techniques. Both complexes presented efficient O-1(2) photogeneration, with anthracenyl-pendant showing higher quantum yields as well as center dot OH production. The DNA photocleavage showed to be dependent on the energy of the exciting radiations thus indicating that the photocleavage process mostly involves the O-1(2) species. In comparison to Ru-Naph, the higher efficiency of the Ru-Anth complex toward the DNA cleavage was assigned to the presence of the anthracenyl moiety that provides an efficient channel to generate O-1(2). These findings have validated the use of conjugated organic ligands with metal complexes as a strategy to bring together binding and photooxidative properties. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.09.034

文献信息

• Ruthenium(II) bipyridine complexes with pendant anthracenyl and naphthyl moieties: A strategy for a ROS generator with DNA binding selectivity
  作者：Felipe Diógenes Abreu、Izaura Cirino Nogueira Diógenes、Luiz Gonzaga de França Lopes、Eduardo Henrique Silva Sousa、Idalina Maria Moreira de Carvalho

  DOI：10.1016/j.ica.2015.09.034

  日期：2016.1

  Coordination compounds that combine selective DNA binding with reactive oxygen species (ROS) generation production have been sought as tools for cell biology studies and cancer therapy. In this respect, the contribution of this work lies on the use of anthracenyl (Ru-Anth) and naphthalyl-pedant (Ru-Naph) ruthenium(II) bipyridine complexes, which were synthesized and fully characterized by spectroscopic and electrochemical techniques. Both complexes presented efficient O-1(2) photogeneration, with anthracenyl-pendant showing higher quantum yields as well as center dot OH production. The DNA photocleavage showed to be dependent on the energy of the exciting radiations thus indicating that the photocleavage process mostly involves the O-1(2) species. In comparison to Ru-Naph, the higher efficiency of the Ru-Anth complex toward the DNA cleavage was assigned to the presence of the anthracenyl moiety that provides an efficient channel to generate O-1(2). These findings have validated the use of conjugated organic ligands with metal complexes as a strategy to bring together binding and photooxidative properties. (C) 2015 Elsevier B.V. All rights reserved.
• Aryl-Substituted Ruthenium(II) Complexes: A Strategy for Enhanced Photocleavage and Efficient DNA Binding
  作者：Felipe Diógenes Abreu、Tercio de F. Paulo、Marcelo H. Gehlen、Rômulo A. Ando、Luiz G. F. Lopes、Ana Cláudia S. Gondim、Mayron A. Vasconcelos、Edson H. Teixeira、Eduardo Henrique Silva Sousa、Idalina Maria Moreira de Carvalho

  DOI：10.1021/acs.inorgchem.7b01108

  日期：2017.8.7

  synthesized two new ruthenium complexes that combine an efficient DNA binding moiety (dppz ligand) together with naphthyl-modified (1) and anthracenyl-modified (2) bipyridine as a strong ROS generator bound to a ruthenium complex. The compounds were fully characterized and their photophysical and photochemical properties investigated. Compound 2 showed one of the highest quantum yields for singlet oxygen

  钌多吡啶复合物已显示出有望用作光动力疗法（PDT）的试剂和分子生物学工具（生色团辅助的光灭活）。为了完成这些任务，重要的是至少要具有目标选择性和巨大的活性氧（ROS）光生能：在同一分子中不容易发现的两个特性。为了制备这种新试剂，我们合成了两种新的钌配合物，它们结合了有效的DNA结合部分（dppz配体）与萘基修饰的（1）和蒽基修饰的（2）联吡啶作为结合到钌配合物上的强ROS产生剂。对该化合物进行了充分表征，并研究了它们的光物理和光化学性质。化合物2表明曾报道为单线态氧产生的最高量子产率中的一个（Φ Δ = 0.96），具有非常高的DNA结合沿（日志ķ b= 6.78）。这种光化学行为可归因于较低的三重态，涉及蒽基修饰的联吡啶，这与较容易的氧猝灭有关。此外，这些化合物对G-四链体DNA表现出中等选择性，并与DNA的小沟结合，这很可能是由侧基配体驱动的。有趣的是，即使暴露于黄色发光二极管（LED