4-[N-(2-anthryl)carbamoyl]-4'-methyl-2,2'-bipyridine | 909867-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-[N-(2-anthryl)carbamoyl]-4'-methyl-2,2'-bipyridine
• 英文别名: 4'-methyl-N-(anthracene-2-yl)-2,2'-bipyridine-4-carboxyamide；4'-methyl-N-(anthracen-2-yl)-2,2'-bipyridine-4-carboxyamide；4′-methyl-N-(anthracene-2-yl)-2,2′-bipyridine-4-carboxyamide；bpyAnth；N-anthracen-2-yl-2-(4-methylpyridin-2-yl)pyridine-4-carboxamide
• CAS: 909867-98-7
• 化学式: C₂₆H₁₉N₃O
• 分子量: 389.456
• InChiKey: IILLTIJFGHNGPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  2,2'-联吡啶 、 4-[N-(2-anthryl)carbamoyl]-4'-methyl-2,2'-bipyridine 、 [(η⁶-C₆H₆)₂RuCl₂Ru(η⁶-C₆H₆)₂] 在 lithium chloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以47%的产率得到[(4-[N-(2-anthryl)carbamoyl]-4'-methyl-2,2'-bipyridine)(2,2'-bipyridine)RuCl₂]
  参考文献：
  名称：

  突破结构多样的光捕集Ru（II）金属有机发色团用于光动力疗法的极限

  摘要：

  Ru（II）衍生物[（AnthbpyMe）（bpy）Ru（dpp）] 2+（2）和[（AnthbpyMe）2 Ru（dpp）] 2+（3）的合成及其激发态性质分析以及它们对神经胶质瘤细胞的光细胞毒性已有报道。配合物2和3吸收带的金属到配位体电荷转移（MLCT）跃迁可见光在λ最大 = 459纳米（16000中号-1 厘米-1）和λ最大 = 461纳米（21000中号-1 厘米-1），分别。配合物表现出双色性质，其中3MLCT发射中心位于λ EM  = 661 nm和λ EM  =对于663纳米2和3分别，而蒽基序（一个或多个）具有450-560 nm发射。蒽单元（一个或多个）淬灭3 MLCT，得到的量子产率（寿命，τ）的Φ EM  = 0.0059（τ  = 398纳秒）和Φ EM  = 0.0011（τ  = 414纳秒）为2和3，分别。淬火率被发现是6.61×10 5 小号-1为2和5.64×10

  DOI：

  10.1016/j.jphotochem.2016.02.006
• 作为产物：
  描述：

  2-氨基蒽 、 4'-甲基-2,2'-联吡啶-4-甲酸 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-[N-(2-anthryl)carbamoyl]-4'-methyl-2,2'-bipyridine
  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

• 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
• Luminescently Tagged 2,2‘-Bipyridine Complex of Fe^II:  Synthesis and Photophysical Studies of 4-[<i>N</i>-(2-Anthryl)carbamoyl]-4‘-methyl-2,2‘-bipyridine
  作者：David F. Zigler、Mark C. Elvington、Julie Heinecke、Karen J. Brewer

  DOI：10.1021/ic060207e

  日期：2006.8.1

  The anthracene lumiphore was linked to the chelating ligand 2,2'-bipyridine, forming 4-[N-(2-anthryl)carbamoyl]-4'-methyl-2,2'-bipyridine (bpyAnth). Coupling through an amide linkage provides some electronic isolation of the anthracene lumiphore. Electrochemistry suggested little change of the anthracene oxidation whether free (1.35 V) linked to 2,2'-bipyridine as bpyAnth (1.30 V) or appended to Fe(II)

  蒽荧光团与螯合配体2，2′-联吡啶连接，形成4- [N-（2-蒽基）氨基甲酰基] -4′-甲基-2，2′-联吡啶（bpyAnth）。通过酰胺键的偶联提供了蒽荧光团的一些电子隔离。电化学表明蒽的氧化变化很小，无论是作为bpyAnth（1.30 V）与2,2'-联吡啶相连的游离（1.35 V）还是与Fe（II）（1.29 V）相连的蒽。bpyAnth配体在375、400、419和441 nm处保留了蒽的结构化发光特性。即使将bpyAnth络合到Fe（II）中心，该蒽的排放也会持续存在。与典型的聚嗪铁（II）配合物形成鲜明对比的是，配合物[Fe（bpyAnth）3] 2+具有发射性。该bpyAnth配体用作2,2'-联吡啶的发光标记类似物，
• 10.1021/acs.inorgchem.4c02235
  作者：Oliveira, Geângela de Fátima Sousa、Gouveia, Florencio Sousa、Andrade, Alexandre Lopes、de Vasconcelos, Mayron Alves、Teixeira, Edson Holanda、Palmeira-Mello, Marcos V.、Batista, Alzir A.、Lopes, Luiz Gonzaga de França、de Carvalho, Idalina Maria Moreira、Sousa, Eduardo Henrique Silva

  DOI：10.1021/acs.inorgchem.4c02235

  日期：——

  properties to be used in photodynamic therapy. Here, we prepared two ruthenium-based compounds with a 2,2′-bipyridine ligand conjugated to an anthracenyl moiety. These compounds coded GRBA and GRPA contain 2,2′-bipyridine or 1,10-phenathroline as auxiliary ligands, respectively, which provide quite a distinct behavior. Notably, compound GRPA exhibited remarkably high photoproduction of singlet oxygen

  金属化合物已成为有前途的新型抗癌剂，它还具有可用于光动力疗法的特性。在这里，我们制备了两种钌基化合物，其 2,2'-联吡啶配体与蒽基部分缀合。这些编码为GRBA和GRPA 的化合物分别含有 2,2'-联吡啶或 1,10-菲咯啉作为辅助配体，它们提供了相当独特的行为。值得注意的是，即使在水中，化合物GRPA也表现出非常高的单线态氧光生成能力 (ψ Δ = 0.96)，几乎是GRBA的两倍 (ψ Δ = 0.52)。另一方面，后者产生的超氧化物和羟基自由基种类是GRPA 的两倍，这可能是由于它们的激发态的调节所致。有趣的是， GRPA表现出与 DNA 的适度结合（ K b = 4.51 × 10 4 ），而GRBA没有表现出仅通过圆二色性测量注意到的可测量的相互作用。对细菌的研究显示出巨大的抗菌作用，包括与商业抗生素组合的协同作用。除此之外， GRBA对四种哺乳动物细胞显示出非常低的细胞毒性或没有细胞毒性，包括难以治疗的
• Pushing the limits of structurally-diverse light-harvesting Ru(II) metal-organic chromophores for photodynamic therapy
  作者：Roberto Padilla、William A. Maza、Anthony J. Dominijanni、Brenda S.J. Winkel、Amanda J. Morris、Karen J. Brewer

  DOI：10.1016/j.jphotochem.2016.02.006

  日期：2016.5

  λem = 663 nm for 2 and 3, respectively, while the anthracene motif(s) has emission from 450–560 nm. The anthracene unit(s) quench the 3MLCT to give quantum yields (lifetime, τ) of Φem = 0.0059 (τ = 398 ns) and Φem = 0.0011 (τ = 414 ns) for 2 and 3, respectively. The quenching rates were found to be 6.61 × 105 s−1 for 2 and 5.64 × 105 s−1 for 3. Electrochemistry reveals an irreversible anthracene oxidation

  Ru（II）衍生物[（AnthbpyMe）（bpy）Ru（dpp）] 2+（2）和[（AnthbpyMe）2 Ru（dpp）] 2+（3）的合成及其激发态性质分析以及它们对神经胶质瘤细胞的光细胞毒性已有报道。配合物2和3吸收带的金属到配位体电荷转移（MLCT）跃迁可见光在λ最大 = 459纳米（16000中号-1 厘米-1）和λ最大 = 461纳米（21000中号-1 厘米-1），分别。配合物表现出双色性质，其中3MLCT发射中心位于λ EM  = 661 nm和λ EM  =对于663纳米2和3分别，而蒽基序（一个或多个）具有450-560 nm发射。蒽单元（一个或多个）淬灭3 MLCT，得到的量子产率（寿命，τ）的Φ EM  = 0.0059（τ  = 398纳秒）和Φ EM  = 0.0011（τ  = 414纳秒）为2和3，分别。淬火率被发现是6.61×10 5 小号-1为2和5.64×10
• 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.