6-Phenylquino<8,7-k><1,8>phenanthroline | 178413-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 6-Phenylquino<8,7-k><1,8>phenanthroline
• 英文别名: 6-phenylquino[8,7-k][1,8]phenanthroline；12-Phenyl-4,13,16-triazapentacyclo[12.8.0.02,11.03,8.015,20]docosa-1,3(8),4,6,9,11,13,15(20),16,18,21-undecaene
• CAS: 178413-47-3
• 化学式: C₂₅H₁₅N₃
• 分子量: 357.414
• InChiKey: KVHZPEZEFFVVEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 顺-双(2,2-二吡啶)二氯化钌(II) 水合物 、 6-Phenylquino<8,7-k><1,8>phenanthroline 以 乙醇 、 水 为溶剂， 以75%的产率得到Ru(bpy)2(6-phenylquino[8,7-k][1,8]phenanthroline)(PF6)2
  参考文献：
  名称：

  [Ru(bpy)₂(L)]Cl₂: Luminescent Metal Complexes That Bind DNA Base Mismatches

  摘要：

  Here we report the synthesis of luminescent ruthenium complexes that bind DNA base pair mismatches. [Ru(bPY)(2)(tpqp)Cl-2 (tpqp = 7,8,13,14-tetrahydro-6-phenylquino[8,7-k][1,8]phenanthroline), [Ru(bPY)(2)(pqp)Cl-2 (pqp = 6-phenylquino[8,7-k][1,8]phenanthroline), and [Ru(bPY)(2)(tactp)]Cl-2 [tactp = 4,5,9,18-tetraazachryseno[9,10-b]triphenylene] have been synthesized, and their spectroscopic proper ties in the absence and presence of DNA have been examined. While [Ru(bPY)(2)(pqp)](2+) Shows no detectable luminescence, [Ru(bPY)(2)(tpqp)](2+) is luminescent in the absence and presence of DNA with an excited-state lifetime of 10 ns and a quantum yield of 0.002, Although no increase in emission intensity is associated with binding to mismatch-containing DNA, luminescence quenching experiments and measurements of steady-state fluorescence polarization provide evidence for preferential binding to oligonucleoticles containing a CC mismatch. Furthermore, by marking the site of binding through singlet oxygen sensitized damage, the complex has been shown to target a CC mismatch site directly with a specific binding affinity, K-b = 4 x 10(6) M-1. [Ru(bPY)(2)(tactp)](2+), an analogue of [Ru(bPY)(2)(dppZ)](2+) containing a bulky intercalating ligand, is luminescent in aqueous solution at micromolar concentrations and exhibits a 12-fold enhancement in luminescence in the presence of DNA, The complex, however, tends to aggregate in aqueous solution; we find a dimerization constant of 9.8 x 10(5) M-1. Again, by singlet oxygen sensitization it is apparent that [Ru(bPY)(2)(tactp)](2+) binds preferentially to a CC mismatch; using a DNase 1 footprinting assay, a binding constant to a CC mismatch of 8 x 10(5) M-1 is found. Hence results with these novel luminescent complexes support the concept of using a structurally demanding ligand to obtain selectivity in targeting single base mismatches in DNA. The challenge is coupling the differential binding we can obtain to differential luminescence.

  DOI：

  10.1021/ic0499291
• 作为产物：
  描述：

  7,8,13,14-Tetrahydro-6-phenylquino<8,7-k><1,8>phenanthroline 在 palladium on activated charcoal 作用下， 反应 3.0h， 以53%的产率得到6-Phenylquino<8,7-k><1,8>phenanthroline
  参考文献：
  名称：

  Keuper, Ralf; Risch, Nikolaus; Floerke, Ulrich, Liebigs Annalen, 1996, # 5, p. 705 - 715

  摘要：

  DOI：