2-(4-(pyridin-2-yl)phenyl)imidazo[4,5-f][1,10]phenanthroline | 1351413-22-3

• 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-(4-(pyridin-2-yl)phenyl)imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-(4-pyridin-2-ylphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline
• CAS: 1351413-22-3
• 化学式: C₂₄H₁₅N₅
• 分子量: 373.417
• InChiKey: FTUYEJNZUADJDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 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：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(2-吡啶基)-苯甲醛 、 1,10-邻二氮杂菲-5,6-二酮 在 ammonium acetate 、 溶剂黄146 作用下， 反应 6.0h， 以58.2%的产率得到2-(4-(pyridin-2-yl)phenyl)imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  The Effects of Grafting of 2-Pyridyl to [Ru(bpy)₂(Hpip)]²⁺on Acid-Base and DNA-Binding Properties: Experimental and DFT Studies

  摘要：

  A new Ru(II) complex of [Ru(bpy)(2)(Hppip)](2+) {bpy = 2,2'-bipyridine; Hppip = 2-(4-(pyridin-2-yl)phenyl)-1H-imidazo[4,5-f][1,10]phenanthroline} has been synthesized by grafting of 2-pyridyl to parent complex [Ru(bpy)(2)(Hpip)](2+) ( Hppip = 2-(4-phenyl)-1H-imidazo[4,5-f] [1,10]phenanthroline). The acid-base properties of [Ru(bpy)(2)(Hppip)](2+) studied by UV-visible and luminescence spectrophotometric pH titrations, revealed off-on-off luminescence switching of [Ru(bpy)(2)(Hppip)](2+) that was driven by the protonation/deprotonation of the imidazolyl and the pyridyl moieties. The complex was demonstrated lobe a DNA intercalator with an intrinsic DNA binding constant of (5.56 +/- 0.2) x 10(5) M-1 in buffered 50 mM NaCl, as evidenced by UV-visible and luminescence titrations, reverse salt effect. DNA competitive binding with ethidium bromide, steady-state emission quenching by [Fe(CN)(6)](4-), DNA melting experiments and viscosity measurements. The density functional theory method was also used to calculate geometric/electronic structures of the complex in an effort to understand the DNA binding properties. All the studies indicated that the introduction of 2-pyridyl onto Hpip ligand is more favorable for extension of conjugate plane of the main ligand than that of phenyl, and for greatly enhanced ct-DNA binding affinity accordingly.

  DOI：

  10.1080/07391102.2011.10508621