10-Methylquinoxalino[2,3-f][1,10]phenanthroline | 220062-39-5

• 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: 10-Methylquinoxalino[2,3-f][1,10]phenanthroline
• CAS: 220062-39-5
• 化学式: C₁₉H₁₂N₄
• 分子量: 296.331
• InChiKey: HEYNOCFSBFAMGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 [Os(1,10-phenanthroline)2Cl₂] 、 10-Methylquinoxalino[2,3-f][1,10]phenanthroline 以 乙二醇 为溶剂， 以70%的产率得到[Os(1,10-phenanthroline)2(6-methyldipyrido[3,2-a:2',3'-c]phenazine)](PF6)2
  参考文献：
  名称：

  Dipyridophenazine Complexes of Os(II) as Red-Emitting DNA Probes:  Synthesis, Characterization, and Photophysical Properties

  摘要：

  Polypyridyl complexes of Os(II) bearing one dipyridophenazine (dppz) derivative and two ancillary ligands derived from bipyridine (bpy) or phenanthroline (phen) exhibit emission maxima at similar to 740 nm and average excited-state lifetimes in the 10 ns range upon binding to DNA by preferential intercalation of the dppz ligand. A family of [Os(L-1)(L-2)(L-3)](2+) and [Os(L-1)(2)(L-2)](2+) complexes with simple modifications in the ancillary phen or bpy ligands (L-1 and L-3) as well as the intercalating dppz ligand (L-2) was prepared. By cyclic voltammetry, electron-donating substituents on the ancillary ligands lowered the Os(3+/2+) reduction potential but did not affect the reduction potential of the dppz ligand. A methyl substituent at the 7-, 8-, or 6-position of the dppz ligand shifted the phenazine reduction toward the negative but did not affect the Os(3+/2+) potential. Absorption titrations indicated intercalative binding to DNA with high affinity (K-B similar to 10(6) M-1) for the family of complexes, although at high ratios (50:1) of base pairs to metal, complexes with ancillary 4,7-dimethylphenanthroline or 4,4'-dimethylbipyridine ligands exhibit less hypochromism (26-27%) in the pi-pi* transition on the dppz ligand compared to complexes with 5,6-dimethylphenanthroline (30-37%) or the parent phen (31-35%). By steady-state and time-resolved emission spectroscopy, complexes bound to DNA by intercalation with substituents on the 4,7- or 4,4'-positions of the ancillary phen or bpy displayed lower quantum yields for emission (Phi(em)) compared to complexes with the parent phen, while complexes with methyl substituents on the dppz ligand had the greatest Phi(em). Studies with poly d(AT), poly d(GC), and mixed-sequence DNA revealed that the emission yields are also sequence-dependent. Comparative luminescence studies in CH2Cl2 demonstrated that these effects arise from a combination of (i) the inherent sensitivity of the excited state to ligand structure and (ii) perturbations in DNA binding geometry introduced by substituents on the ancillary and intercalating ligands. Our results clarify the relationships between ligand architecture and emission yield and lifetime in the presence and absence of DNA and illustrate the utility of dppz complexes of Os(II) as luminescent probes for DNA.

  DOI：

  10.1021/ic9808955
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 、 2,3-二氨基甲苯 以 乙醇 为溶剂， 生成 10-Methylquinoxalino[2,3-f][1,10]phenanthroline
  参考文献：
  名称：

  一种用于抑制隐球菌的吩嗪类钌（Ⅱ）配合物六氟磷酸盐及其制备方法和应用

  摘要：

  本发明公开了一种用于抑制隐球菌的吩嗪类钌(Ⅱ)配合物六氟磷酸盐及其制备方法和应用，本发明中的盐以钌金属离子为核心，以1,10‑菲啰啉或联吡啶及其衍生物为骨架配体，以DPPZ‑F,Cl、DPPZ‑Cl、DPPZ‑Me和BPPX为结合配体，其性质稳定，对新生隐球菌具有良好的抗菌活性。该盐可以和药学可以接受的载体或赋形剂混合制备成抗真菌药物。该盐合成步骤短，设备技术条件和工艺流程简单，原材料来源充裕，适合扩大化生产。

  公开号：

  CN115583978A

文献信息

• Dipyridophenazine Complexes of Os(II) as Red-Emitting DNA Probes:  Synthesis, Characterization, and Photophysical Properties
  作者：R. Erik Holmlin、Johanna A. Yao、Jacqueline K. Barton

  DOI：10.1021/ic9808955

  日期：1999.1.1

  Polypyridyl complexes of Os(II) bearing one dipyridophenazine (dppz) derivative and two ancillary ligands derived from bipyridine (bpy) or phenanthroline (phen) exhibit emission maxima at similar to 740 nm and average excited-state lifetimes in the 10 ns range upon binding to DNA by preferential intercalation of the dppz ligand. A family of [Os(L-1)(L-2)(L-3)](2+) and [Os(L-1)(2)(L-2)](2+) complexes with simple modifications in the ancillary phen or bpy ligands (L-1 and L-3) as well as the intercalating dppz ligand (L-2) was prepared. By cyclic voltammetry, electron-donating substituents on the ancillary ligands lowered the Os(3+/2+) reduction potential but did not affect the reduction potential of the dppz ligand. A methyl substituent at the 7-, 8-, or 6-position of the dppz ligand shifted the phenazine reduction toward the negative but did not affect the Os(3+/2+) potential. Absorption titrations indicated intercalative binding to DNA with high affinity (K-B similar to 10(6) M-1) for the family of complexes, although at high ratios (50:1) of base pairs to metal, complexes with ancillary 4,7-dimethylphenanthroline or 4,4'-dimethylbipyridine ligands exhibit less hypochromism (26-27%) in the pi-pi* transition on the dppz ligand compared to complexes with 5,6-dimethylphenanthroline (30-37%) or the parent phen (31-35%). By steady-state and time-resolved emission spectroscopy, complexes bound to DNA by intercalation with substituents on the 4,7- or 4,4'-positions of the ancillary phen or bpy displayed lower quantum yields for emission (Phi(em)) compared to complexes with the parent phen, while complexes with methyl substituents on the dppz ligand had the greatest Phi(em). Studies with poly d(AT), poly d(GC), and mixed-sequence DNA revealed that the emission yields are also sequence-dependent. Comparative luminescence studies in CH2Cl2 demonstrated that these effects arise from a combination of (i) the inherent sensitivity of the excited state to ligand structure and (ii) perturbations in DNA binding geometry introduced by substituents on the ancillary and intercalating ligands. Our results clarify the relationships between ligand architecture and emission yield and lifetime in the presence and absence of DNA and illustrate the utility of dppz complexes of Os(II) as luminescent probes for DNA.
• 一种用于抑制隐球菌的吩嗪类钌（Ⅱ）配合物六氟磷酸盐及其制备方法和应用
  申请人：西南大学

  公开号：CN115583978A

  公开（公告）日：2023-01-10

  本发明公开了一种用于抑制隐球菌的吩嗪类钌(Ⅱ)配合物六氟磷酸盐及其制备方法和应用，本发明中的盐以钌金属离子为核心，以1,10‑菲啰啉或联吡啶及其衍生物为骨架配体，以DPPZ‑F,Cl、DPPZ‑Cl、DPPZ‑Me和BPPX为结合配体，其性质稳定，对新生隐球菌具有良好的抗菌活性。该盐可以和药学可以接受的载体或赋形剂混合制备成抗真菌药物。该盐合成步骤短，设备技术条件和工艺流程简单，原材料来源充裕，适合扩大化生产。