2-(5'-phenylfuran-2'-yl)-1H-imidazo[4,5-f][1,10]phenanthroline | 1357392-28-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2-(5'-phenylfuran-2'-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-(5-phenylfuran-2-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
• CAS: 1357392-28-9
• 化学式: C₂₃H₁₄N₄O
• 分子量: 362.39
• InChiKey: KBDLLNXRGYFGAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 顺-双(2,2'-二吡啶基)二氯化钌(II)二水合物 、 2-(5'-phenylfuran-2'-yl)-1H-imidazo[4,5-f][1,10]phenanthroline 以 乙二醇 为溶剂， 以96%的产率得到[Ru(bpy)2(2-(5'-phenylfuran-2'-yl)-1H-imidazo[4,5-f][1,10]phenanthroline)](PF6)2
  参考文献：
  名称：

  Pedras, Bruno; Batista, Rosa M. F.; Tormo, Laura, Inorganica Chimica Acta

  摘要：

  DOI：
• 作为产物：
  描述：

  5-苯基-2-糠醛 、 1,10-邻二氮杂菲-5,6-二酮 在 ammonium acetate 、 溶剂黄146 、 ammonium hydroxide 作用下， 反应 5.0h， 以60%的产率得到2-(5'-phenylfuran-2'-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  Synthesis, characterization, photophysical studies and interaction with DNA of a new family of Ru(II) furyl- and thienyl-imidazo-phenanthroline polypyridyl complexes

  摘要：

  A new family of Ru(II) polypyridyl complexes (C1 to C6) containing furyl- or thienyl-imidazo-phenanthroline ligands (4-6) were synthesized using microwave irradiation and characterized by elemental analysis, H-1 NMR, UV-Vis absorption and fluorescence spectroscopy, FAB, ESI-MS and MALDI-TOF-MS spectrometry. On the other hand, the novel furyl-or thienyl-imidazo-phenanthroline derivatives (5-6) were synthesized through the Radziszewski reaction and completely characterized by the usual spectroscopic techniques. The interaction of the complexes with calf thymus DNA in the absence and in the presence of different quenchers (ethidium bromide, potassium hexacyanoferrate(II) and methyl viologen) has been studied by absorption spectroscopy, steady-state and single-photon timing luminescence measurements. Their electronic spectra show visible absorption peaks at 457-463 nm, with red luminescence at 603-613 nm. The emission quantum yields of these complexes are between 0.006 and 0.016 in air-equilibrated DMSO solution. Luminescence lifetimes in water lie within the 0.4-1.0 mu s range, with a non-exponential behavior due to aggregation of the probe. Ru(II) complexes C3, C4, C5 and C6 show intrinsic dsDNA-binding constants of 2.74 x 10(5), 3.02 x 10(5), 1.32 x 10(5) and 1.63 x 10(5) M (1), respectively. The planar extended structure of the imidazo-phenanthroline ligands and the collected spectroscopic data suggest a partial intercalative binding mode of the novel metal probes to double-stranded DNA. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.07.020

文献信息

• Pedras, Bruno; Batista, Rosa M. F.; Tormo, Laura, Inorganica Chimica Acta
  作者：Pedras, Bruno、Batista, Rosa M. F.、Tormo, Laura、Costa, Susana P. G.、Raposo, M. Manuela M.、et al.

  DOI：——

  日期：——
• Synthesis, characterization, photophysical studies and interaction with DNA of a new family of Ru(II) furyl- and thienyl-imidazo-phenanthroline polypyridyl complexes
  作者：Bruno Pedras、Rosa M.F. Batista、Laura Tormo、Susana P.G. Costa、M. Manuela M. Raposo、Guillermo Orellana、José Luís Capelo、Carlos Lodeiro

  DOI：10.1016/j.ica.2011.07.020

  日期：2012.2

  A new family of Ru(II) polypyridyl complexes (C1 to C6) containing furyl- or thienyl-imidazo-phenanthroline ligands (4-6) were synthesized using microwave irradiation and characterized by elemental analysis, H-1 NMR, UV-Vis absorption and fluorescence spectroscopy, FAB, ESI-MS and MALDI-TOF-MS spectrometry. On the other hand, the novel furyl-or thienyl-imidazo-phenanthroline derivatives (5-6) were synthesized through the Radziszewski reaction and completely characterized by the usual spectroscopic techniques. The interaction of the complexes with calf thymus DNA in the absence and in the presence of different quenchers (ethidium bromide, potassium hexacyanoferrate(II) and methyl viologen) has been studied by absorption spectroscopy, steady-state and single-photon timing luminescence measurements. Their electronic spectra show visible absorption peaks at 457-463 nm, with red luminescence at 603-613 nm. The emission quantum yields of these complexes are between 0.006 and 0.016 in air-equilibrated DMSO solution. Luminescence lifetimes in water lie within the 0.4-1.0 mu s range, with a non-exponential behavior due to aggregation of the probe. Ru(II) complexes C3, C4, C5 and C6 show intrinsic dsDNA-binding constants of 2.74 x 10(5), 3.02 x 10(5), 1.32 x 10(5) and 1.63 x 10(5) M (1), respectively. The planar extended structure of the imidazo-phenanthroline ligands and the collected spectroscopic data suggest a partial intercalative binding mode of the novel metal probes to double-stranded DNA. (C) 2011 Elsevier B.V. All rights reserved.