3-(1,10-phenanthrolin-2-yl)-as-triazino[5,6-f]naphthalene | 1403965-51-4

• 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: 3-(1,10-phenanthrolin-2-yl)-as-triazino[5,6-f]naphthalene
• 英文别名: 2-(1,10-Phenanthrolin-2-yl)benzo[f][1,2,4]benzotriazine；2-(1,10-phenanthrolin-2-yl)benzo[f][1,2,4]benzotriazine
• CAS: 1403965-51-4
• 化学式: C₂₃H₁₃N₅
• 分子量: 359.39
• InChiKey: IGGSPKWMWMQGBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：
  64.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,2-萘醌 、 1,10-phenanthroline-₂-carbohydrazonamide 以 乙醇 为溶剂， 反应 6.0h， 以78%的产率得到3-(1,10-phenanthrolin-2-yl)-as-triazino[5,6-f]naphthalene
  参考文献：
  名称：

  Synthesis, characterization, and DNA-binding studies of ruthenium complexes [Ru(tpy)(ptn)]2+ and Ru(dmtpy)(ptn)]2+

  摘要：

  Two ruthenium(II) polypyridyl complexes [Ru(tpy)(ptn)](2+) (1) and Ru(dmtpy)(ptn)](2+) (2) (ptn = 3-(1,10-phenanthrolin-2-yl)-as-triazino[5,6-f]naphthalene, tpy = 2,2':6',2 ''-terpyridine, dmtpy = 5,5'-dimethyl-2,2':6',2 ''-terpyridine) have been synthesized and characterized by elemental analysis, H-1 NMR, mass spectrometry and crystal structure analysis. Spectroscopic studies together with isothermal titration calorimetry (ITC) and viscosity measurements prove that two complexes bind to DNA in an intercalative mode. ITC experiments show that the binding mode for complex 2 is entropically driven, while an entropy-driven initial binding of complex 1 is followed by an entropically and enthalpically favorable process. This difference may be attributed to the ancillary ligand effects on the DNA binding of Ru(II) complexes. Circular dichroism titrations of calf thymus DNA (CT-DNA) with Ru(II) complexes show that complexes 1 and 2 induce B to Z conformational transition of calf thymus DNA at low ionic strength (0.05 M NaCl). The induced Z-DNA conformation can revert to B form when Ru(II) complexes are displaced by ethidium bromide or at high ionic strengths ([NaCl] = 0.4 M), but keeps intact with temperature ranged from 25 to 90 degrees C. The unique structure and characteristics of Ru(II) complexes designed in this investigation will be useful for the study of Z-DNA. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2012.03.008

文献信息

• Synthesis, characterization, and DNA-binding studies of ruthenium complexes [Ru(tpy)(ptn)]2+ and Ru(dmtpy)(ptn)]2+
  作者：Lü-Ying Li、Hai-Na Jia、Hui-Juan Yu、Ke-Jie Du、Qi-Tian Lin、Kang-Qiang Qiu、Hui Chao、Liang-Nian Ji

  DOI：10.1016/j.jinorgbio.2012.03.008

  日期：2012.8

  Two ruthenium(II) polypyridyl complexes [Ru(tpy)(ptn)](2+) (1) and Ru(dmtpy)(ptn)](2+) (2) (ptn = 3-(1,10-phenanthrolin-2-yl)-as-triazino[5,6-f]naphthalene, tpy = 2,2':6',2 ''-terpyridine, dmtpy = 5,5'-dimethyl-2,2':6',2 ''-terpyridine) have been synthesized and characterized by elemental analysis, H-1 NMR, mass spectrometry and crystal structure analysis. Spectroscopic studies together with isothermal titration calorimetry (ITC) and viscosity measurements prove that two complexes bind to DNA in an intercalative mode. ITC experiments show that the binding mode for complex 2 is entropically driven, while an entropy-driven initial binding of complex 1 is followed by an entropically and enthalpically favorable process. This difference may be attributed to the ancillary ligand effects on the DNA binding of Ru(II) complexes. Circular dichroism titrations of calf thymus DNA (CT-DNA) with Ru(II) complexes show that complexes 1 and 2 induce B to Z conformational transition of calf thymus DNA at low ionic strength (0.05 M NaCl). The induced Z-DNA conformation can revert to B form when Ru(II) complexes are displaced by ethidium bromide or at high ionic strengths ([NaCl] = 0.4 M), but keeps intact with temperature ranged from 25 to 90 degrees C. The unique structure and characteristics of Ru(II) complexes designed in this investigation will be useful for the study of Z-DNA. (C) 2012 Elsevier Inc. All rights reserved.