2-(2-bromophenyl)imidazo[4,5-f]-1,10-phenanthroline | 614717-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(2-bromophenyl)imidazo[4,5-f]-1,10-phenanthroline
• 英文别名: 2-(2-Bromophenyl)-1h-imidazo[4,5-f][1,10]phenanthroline；2-(2-bromophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline
• CAS: 614717-88-3
• 化学式: C₁₉H₁₁BrN₄
• 分子量: 375.227
• InChiKey: ROIFAXSCIBHRLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-乙基苯乙炔 、 2-(2-bromophenyl)imidazo[4,5-f]-1,10-phenanthroline 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 以81%的产率得到15-(4-ethylphenyl)isoquinolino[2',1':1,2]imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  铜（I）/邻苯二酚催化合成15-芳基异喹啉并[2'，1'：1,2]咪唑并[4,5-f] [1,10]菲咯啉

  摘要：

  通过铜（I）催化2-（2-溴苯基）反应合成了一系列的15-芳基异喹啉基[2'，1'：1,2，]咪唑并[4,5- f ] [1,10]菲咯啉在Cs 2 CO 3存在下，-1 H-咪唑并[4,5- f ] [1,10]菲咯啉和末端炔烃。事实证明，这是一种有效的合成带有三种杂环的六环化合物的有效方法，这些杂环是异喹啉，咪唑和菲咯啉。 图形摘要 通过2-（2-溴苯基）-1H-的铜（I）催化合成15-芳基异喹啉基[2'，1'：1,2，]咪唑并[4,5- f ] [1,10]菲咯啉在Cs 2 CO 3存在下，咪唑并[4,5- f ] [1,10]菲咯啉和末端炔烃。

  DOI：

  10.1007/s11164-021-04395-w
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 、 邻溴苯甲醛 在 乙酸铵 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以78%的产率得到2-(2-bromophenyl)imidazo[4,5-f]-1,10-phenanthroline
  参考文献：
  名称：

  Effects of ligand planarity on the interaction of polypyridyl Ru(ii) complexes with DNA

  摘要：

  两个在苯环不同位置含有取代基 Br 的新聚吡啶基配体，OBIP {OBIP = 2-(2-溴苯基)咪唑并[4,5-f]-1,10-菲咯啉}，PBIP {PBIP = 2-(4 -溴苯基)咪唑并[4,5-f]-1,10-菲咯啉}及其 Ru(II) 配合物，[Ru(dmp)2(OBIP)]2+1 和 [Ru(dmp)2(PBIP)] 2+2 （dmp = 2,9-二甲基-1,10-菲咯啉）已合成并表征。通过分光光度法、粘度测量以及平衡透析和圆二色光谱法研究了两种复合物与小牛胸腺 DNA (CT DNA) 的结合。还应用密度泛函理论（DFT）方法对这两种配合物进行了理论计算。配合物1的结构已通过单晶X射线衍射技术确定。咪唑并[4,5-f]-1,10-菲咯啉部分与2-溴苯环不共面，在OBIP配体中具有48.6°的二面角。理论计算进一步证实了这种扭曲构象，其中二面角为48.2°。理论计算还表明配合物2中的PBIP配体基本上是平面的（二面角为0.4°）。实验结果表明，复合物1通过半嵌入模式与CT DNA结合，而复合物2通过嵌入模式与CT DNA强烈结合。因此，与复合物 1 相比，复合物 2 是 CT DNA 对映选择性结合剂更好的候选者。理论结果已经合理地解释了一些实验规律或趋势。这表明插层配体的平面性对配合物的光谱性质和DNA结合行为有显着影响，DFT方法可以有效地解释和预测聚吡啶Ru( II) 与DNA的复合物。

  DOI：

  10.1039/b300353a

文献信息

• 一种芳烃钌配合物及其制备方法与应用
  申请人：广东药科大学

  公开号：CN107793454B

  公开（公告）日：2020-05-05

  本发明公开了一种芳烃钌配合物，采用R1R2R3PIP为主配体，所述R1、R2、R3独立地选自‑Cl,‑F,‑Br,‑I,‑CF3,‑NO2,‑OCH3,‑OH,‑COOH,‑CH3,‑N(CH3)2,‑C2H2,‑SO2CH3、碳原子数为1～6的烷基或碳原子为1～6的取代烷基、吡啶基或取代吡啶基、呋喃基或取代呋喃基、吡咯基或取代吡咯基、噻唑或取代噻唑基；其中，所述苯基、吡啶基、呋喃基、噻唑的取代基均独立的选自羟基、硝基、卤素、氨基、羧基、氰基、巯基、碳原子数为3～8的环烷基、SO3H、碳原子数为1～6的烷基、碳原子数为2～6的链烯基、碳原子为2～6的链炔基、羟基(C1‑C6)烷基、氨基(C1‑C6)烷基、CO2R’、CONR’R’、COR’、SO2R’R’、(C1‑C6)烷氧基、(C1‑C6)烷硫基、‑N＝NR’、NR’R’或三氟(C1‑C6)烷基中的任一种。
• Microwave-assisted synthesis of phenanthroimidazole derivatives as stabilizer of c-myc G-quadruplex DNA
  作者：Siyan Liao、Zhao Zhang、Qiong Wu、Xicheng Wang、Wenjie Mei

  DOI：10.1016/j.bmc.2014.09.003

  日期：2014.11

  c-myc G-quadruplex DNA, which plays a central role in tumor progression and resistance, has been extensively investigated as potential target of antitumor drugs. In this paper, a series of phenanthroimidazole derives have been synthesized under irradiation of microwave in yields of 51-80%. The antitumor activity of these compounds against various tumor cells has been evaluated, and the results show that these compounds exhibit great inhibition to MDA-MB-231, MCF-7 and Hela cells, especially 5 inhibit the growth of MDA-MB-231 cells with IC50 about 3.6 mu M. The further studies show that 5 can bind and stabilize c-myc G4 DNA in pi-pi stacking mode, which confirmed by the hypochromise in the electronic spectra of 5 with the increasing of c-myc G4 DNA. When dealt with 5, the strength of CD signal attributed to c-myc G4 DNA is decreased and the FRET melting point of c-myc G4 DNA is increased. Moreover, the molecule docking calculation was conducted to show that 5 suitably stack onto the 50 G-quartet surface, and parallels to the surfaces of the G5 and G-quartet consisting of G7, G11, G16, and G20. As a result, the replication of c-myc oligomers is blocked by 5. In a word, this type of phenanthroimidazole derives can act as potential inhibitor against breast cancer cells by binding and stabilizing c-myc G4 DNA through p-p stacking. (C) 2014 Elsevier Ltd. All rights reserved.
• Xu, Hong; Zheng, Kang-Cheng; Chen, Yao, Dalton Transactions
  作者：Xu, Hong、Zheng, Kang-Cheng、Chen, Yao、Li, Yi-Zhi、Lin, Li-Jun、et al.

  DOI：——

  日期：——
• Synthesis of 15-Arylisoquinolino[2′,1′:1,2] imidazo[4,5-f][1,10]phenanthrolines catalyzed by Copper(I)/o-Phen
  作者：Mei-Mei Zhang、Tuan-Jie Li、Jian-Quan Liu、Xiang-Shan Wang

  DOI：10.1007/s11164-021-04395-w

  日期：2021.5

  15-arylisoquinolino[2′,1′:1,2]imidazo[4,5-f][1,10]phenanthrolines was synthesized by a copper(I)-catalyzed reaction of 2-(2-bromophenyl)-1H-imidazo[4,5-f][1,10] phenanthrolines and terminal alkyne in the presence of Cs2CO3. It was proved to be an efficient method for the synthesis of hexacyclic compounds bearing three kinds of heterocycles which were isoquinoline, imidazole and phenanthroline. Graphic abstract

  通过铜（I）催化2-（2-溴苯基）反应合成了一系列的15-芳基异喹啉基[2'，1'：1,2，]咪唑并[4,5- f ] [1,10]菲咯啉在Cs 2 CO 3存在下，-1 H-咪唑并[4,5- f ] [1,10]菲咯啉和末端炔烃。事实证明，这是一种有效的合成带有三种杂环的六环化合物的有效方法，这些杂环是异喹啉，咪唑和菲咯啉。 图形摘要 通过2-（2-溴苯基）-1H-的铜（I）催化合成15-芳基异喹啉基[2'，1'：1,2，]咪唑并[4,5- f ] [1,10]菲咯啉在Cs 2 CO 3存在下，咪唑并[4,5- f ] [1,10]菲咯啉和末端炔烃。
• Effects of ligand planarity on the interaction of polypyridyl Ru(ii) complexes with DNA
  作者：Hong Xu、Kang-Cheng Zheng、Yao Chen、Yi-Zhi Li、Li-Jun Lin、Hong Li、Pei-Xin Zhang、Liang-Nian Ji

  DOI：10.1039/b300353a

  日期：——

  Two new polypyridyl ligands containing substituent Br at different positions in the phenyl ring, OBIP OBIP = 2-(2-bromophenyl)imidazo[4,5-f]-1,10-phenanthroline}, PBIP PBIP = 2-(4-bromophenyl)imidazo[4,5-f]-1,10-phenanthroline} and their Ru(II) complexes, [Ru(dmp)2(OBIP)]2+1 and [Ru(dmp)2(PBIP)]2+2 (dmp = 2,9-dimethyl-1,10-phenanthroline), have been synthesized and characterized. The binding of the two complexes to calf thymus DNA (CT DNA) has been investigated by spectrophotometric methods, viscosity measurements, as well as equilibrium dialysis and circular dichroism spectroscopy. Theoretical calculations for the two complexes were also carried out applying the density functional theory (DFT) method. The structure of complex 1 has been determined by single-crystal X-ray diffraction techniques. The imidazo[4,5-f]-1,10-phenanthroline moiety is not coplanar with the 2-bromophenyl ring, having a dihedral angle of 48.6° in the OBIP ligand. The twisted conformation has been further confirmed by theoretical calculations, in which this dihedral angle is 48.2°. The theoretical calculations also suggest that the PBIP ligand in complex 2 is essentially planar (dihedral angle is 0.4°). The experimental results show that while complex 1 binds to CT DNA via a semi-intercalative mode, complex 2 strongly binds to CT DNA through intercalation. Complex 2 is thus a much better candidate as an enantioselective binder to CT DNA than complex 1. Some experimental regularities or trends have been reasonably explained by the theoretical results. These suggest that the planarity of the intercalated ligand has significant effects on the spectral properties and the DNA-binding behavior of the complexes, and that the DFT method can be used effectively to explain and predict some regularities or trends in the interaction of polypyridyl Ru(II) complexes with DNA.

  两个在苯环不同位置含有取代基 Br 的新聚吡啶基配体，OBIP OBIP = 2-(2-溴苯基)咪唑并[4,5-f]-1,10-菲咯啉}，PBIP PBIP = 2-(4 -溴苯基)咪唑并[4,5-f]-1,10-菲咯啉}及其 Ru(II) 配合物，[Ru(dmp)2(OBIP)]2+1 和 [Ru(dmp)2(PBIP)] 2+2 （dmp = 2,9-二甲基-1,10-菲咯啉）已合成并表征。通过分光光度法、粘度测量以及平衡透析和圆二色光谱法研究了两种复合物与小牛胸腺 DNA (CT DNA) 的结合。还应用密度泛函理论（DFT）方法对这两种配合物进行了理论计算。配合物1的结构已通过单晶X射线衍射技术确定。咪唑并[4,5-f]-1,10-菲咯啉部分与2-溴苯环不共面，在OBIP配体中具有48.6°的二面角。理论计算进一步证实了这种扭曲构象，其中二面角为48.2°。理论计算还表明配合物2中的PBIP配体基本上是平面的（二面角为0.4°）。实验结果表明，复合物1通过半嵌入模式与CT DNA结合，而复合物2通过嵌入模式与CT DNA强烈结合。因此，与复合物 1 相比，复合物 2 是 CT DNA 对映选择性结合剂更好的候选者。理论结果已经合理地解释了一些实验规律或趋势。这表明插层配体的平面性对配合物的光谱性质和DNA结合行为有显着影响，DFT方法可以有效地解释和预测聚吡啶Ru( II) 与DNA的复合物。