5-硝基-6氨基-1,10-邻菲罗啉 | 168646-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 中文名称: 5-硝基-6氨基-1,10-邻菲罗啉
• 中文别名: 5-硝基-6-氨基-1,10-菲罗啉
• 英文名称: 5-amino-6-nitro-1,10-phenanthroline
• 英文别名: 5-nitro-6-amino-1,10-phenanthroline；5-nitro-6-amino phenanthroline；6-nitro-1,10-phenanthrolin-5-amine
• CAS: 168646-53-5
• 化学式: C₁₂H₈N₄O₂
• 分子量: 240.221
• InChiKey: FPDWWTWQUVUMJH-UHFFFAOYSA-N

物化性质

• 沸点：
  510.9±45.0 °C(Predicted)
• 密度：
  1.518±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.6
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-硝基-6氨基-1,10-邻菲罗啉 生成 1,10-邻二氮杂菲-5,6-二酮
  参考文献：
  名称：

  Low Quantum Yields of Relaxed Electron Transfer Products of Moderately Coupled Ruthenium(II)−Cobalt(III) Compounds on the Subpicosecond Laser Excitation

  摘要：

  Photoinduced electron-transfer reactions of [(tpy)Ru-II(tpy-tpy)Co-III(tpy)]5+ (tpy = 2,2':6',2"-terpyridine and tpy-tpy = 6',6"-bis(2-pyridyl)-2,2':4',4":2",2"'-quarterpyridyne), [(tpy)Ru-II(tpy-ph-tpy)Co-III(tpy)](5+) (tpy-ph-tpy = 1,4-bis[2,2':6',2"-terpyridine-4'-yl]benzene), and [(bpy)(2)Ru-II(tpphz)Co-III(bpy)(2)](5+) (bpy = 2,2'-bipyridine, and tpphz = tetrapyrido[3,2-a:2',3'-c:3",2"-h::2"',3"'-j]phenazine) were studied in the range 140-298 K by means of subpicosecond transient absorption spectroscopy. (MLCT)-M-3(Ru) of [(tpy)Ru-II(L-L)Co-III(tpy)](5+) (L-L: tpy-tpy and tpy-ph-tpy) underwent intramolecular electron-transfer (EET) reaction to form [Ru-2(III)(tpy)(L-L)Co-2(II)(tpy)](5+) in a shorter time than 10 ps. Low quantum yields of the EET products (0.53 for tpy-tpy and 0.41 for tpy-ph-tpy in butyronitrile at 298 K) measured before the fast return electron-transfer were found as in the intermolecular electron-transfer quenching of (MLCT)-M-3(Ru) by [Co(tpy)(2)](3+). The quantum yield of [(tpy)-Ru-II(tpy-tpy)Co-II(tpy)](5+) (Phi) decreases to 0.38 in a slowly reorganizing solvent of propylene carbonate and that of [(tpy)Ru-II(tpy-ph-tpy)Co-III(tpy)](5+) to 0.21 at 180 K. The reductions in the EET yields, 1 - Phi, can be ascribed to a fast transition of the nonrelaxed EET product to the lowest triplet d-d* state of [Co-III(tpy)(2)] moiety during the solvent reorganization. A tunneling transition of the nonrelaxed EET products to the lowest lying d-d excited-state of [Co-III(tpy)(2)] moiety takes place as a hole transfer, HT, from the dpi-orbital of Ru(III) to that of Co(II) with a configuration of dpi(6)dsigma*. An electronic coupling of dpi(Ru)-dpi(Co) estimated from the intensity of inter-valence transition of [(tpy)Ru-III(L-L)Ru-II(tpy)](5+) (Collin, J.-P.; Laine, P.; Launay, J.-P.; Sauvage, J.-P.; Sour, A. J. Chem. Soc., Chem. Commun. 1993, 434) is large enough to carry out the HT. The weak coupling of dpi(Ru)-dpi(Co) in the case of [(bpy)(2)Ru(tpphz)Co(bpy)(2)](5+) attenuates the HT rate to bring about a high yield of EET (0.8). The possibility that energy-transfer of (MLCT)-M-3(Ru) to the Co(III) moiety via an intermediate super-exchange coupling between dpi(Ru) and dpi(Co) occurs in competition with the EET of [(tpy)Ru-III(tpy-ph-tpy)Co-II(tpy)](5+) is also pursued.

  DOI：

  10.1021/jp037259z
• 作为产物：
  描述：

  1,10-菲罗啉 在 硫酸 、 盐酸羟胺 、 硝酸 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.25h， 生成 5-硝基-6氨基-1,10-邻菲罗啉
  参考文献：
  名称：

  灵活的RuII Schiff碱基复合物：G-四链体DNA结合和光诱导的癌细胞死亡。

  摘要：

  已经制备了一系列基于马参部分的新的Ru II Schiff碱复合物。其中包括四种包含Ni II，Pd II或Pt II的柔性单金属Ru II化合物和六个刚性双金属类似物阳离子进入丹参络合位点。稳态发光滴定表明该化合物具有光探针G-四链体（G4）DNA的能力。此外，席夫碱的大量结构变化允许广泛评估配体表面，柔性和电荷对化合物与G4 DNA相互作用的影响。这要归功于圆二色谱熔融分析和生物层干涉法研究，这些研究指出了Ru II Schiff碱基配合物对G4 DNA的高亲和力和良好的选择性。在纤维素用最有前途的化合物进行了研究。观察到化合物在核以及在核仁中的细胞摄取。在黑暗和光照射下，用U2OS骨肉瘤细胞进行细胞活力实验，从而可以测量IC 50值和光指数。他们显示了光照射除了在黑暗中分子的低细胞毒性外，还对药物的活性发挥了重要作用。总之，报告的结果强调了Ru II Schiff碱基复合物作为开发潜在的靶向诊断或治疗化合物的G4

  DOI：

  10.1002/chem.202001409

文献信息

• Two structurally analogous ruthenium complexes as naked-eye and reversible molecular “light switch” for G-quadruplex DNA
  作者：Xiao-Hui Lu、Shuo Shi、Jun-Liang Yao、Xing Gao、Hai-Liang Huang、Tian-Ming Yao

  DOI：10.1016/j.jinorgbio.2014.07.003

  日期：2014.11

  that both Ru-complexes exhibited a remarkable “light switch” effect in the presence of hybrid G-quadruplex DNA. Interestingly, the “light switch” can be repeated off and on through the successive addition of Cu2 + ions and EDTA, and all these behaviors can be observed even by the naked eyes. Moreover, FRET melting assay revealed that both complexes could be potential stabilizers for G-quadruplex architectures

  一对对称的呋喃基钌（II）络合物（[Ru（phen）2 dpq-df] 2 +（1）和[Ru（bpy）2 dpq-df] 2 +（2）（phen = 1,10-菲咯啉，bpy = 2,2'-联吡啶，dpq-df = dipyrido（3,2-a：2'，3'-c）喹喔啉-二呋喃）已经制备并表征。已经通过荧光光谱，UV-Vis光谱，圆二色性（CD），荧光共振能量转移（FRET）熔解分析和分子对接研究研究了两种复合物对G-四链体DNA的结合特性。实验结果表明，在存在杂合G-四链体DNA的情况下，两种Ru复合体均表现出显着的“光开关”效果。有趣的是，可以通过连续添加Cu 2 +来反复打开和关闭“电灯开关”。离子和EDTA，所有这些行为都可以通过肉眼观察到。此外，FRET熔解分析表明，两种复合物都可能是G-四链体结构的潜在稳定剂。计算研究不仅证实了这两个复杂分子与一个G四联体DNA分子结合，而且还解释了“光开关”效应。
• Stepwise syntheses of mono- and di-nuclear ruthenium tpphz complexes [(bpy)₂Ru(tpphz)]^2–and [(bpy)₂Ru(tpphz)Ru(bpy)₂]⁴⁺{tpphz = tetrapyrido[3,2-a: 2′,3′-c: 3″,2″-h: 2″,3‴-j]phenazine}
  作者：Joseph Bolger、André Gourdon、Eléna Ishow、Jean-Pierre Launay

  DOI：10.1039/c39950001799

  日期：——

  The complex [(bpy)2Ru(tpphz)]2+(tpphz = tetrapyridophenazine), is obtained by reaction of [(bpy)2Ru(phendione)]2+with 5,6-diamino-1,10-phenanthroline; upon reaction with [(bpy)2Ru(Me2CO)2]2+, the fully conjugated dimer [(bpy)2Ru(tpphz)Ru(bpy)2]4+ is obtained.

  复杂物[(bpy)2Ru(tpphz)]2+（tpphz = 四吡啶苯啶）是通过[(bpy)2Ru(phendione)]2+与5,6-二氨基-1,10-菲啰啉反应获得的；与[(bpy)2Ru(Me2CO)2]2+反应后，得到完全共轭的二聚体[(bpy)2Ru(tpphz)Ru(bpy)2]4+。
• Synthesis of Novel Substituted 1,10-Phenanthrolines
  作者：Heather Camren、Mei-Yueh Chang、Liansheng Zeng、Mark E. McGuire

  DOI：10.1080/00397919608003733

  日期：1996.3

  Abstract The syntheses of both 5-amino-6-nitro-1,10-phenanthroline and 5,6-diamino-1,10-phenanthroline (starting from 5-nitro-1,10-phenanthroline) are described in detail.

  摘要 详细描述了5-氨基-6-硝基-1,10-菲咯啉和5,6-二氨基-1,10-菲咯啉（以5-硝基-1,10-菲咯啉为原料）的合成。
• DNA binding and cleavage properties of a newly synthesised Ru(II)-polypyridyl complex
  作者：Amrita Ghosh、Amit Mandoli、D. Krishna Kumar、Narendra Singh Yadav、Tamal Ghosh、Bhavanath Jha、Jim A. Thomas、Amitava Das

  DOI：10.1039/b906756f

  日期：——

  The single crystal X-ray structure of the newly synthesized ruthenium (II)-polypyridyl complex, [(bpy)(2)Ru(L)](PF(6))(2) (1) (bpy is 2,2'-bipyridyl and L is 2-methyl-2H-1,3,7,8-tetraaza-cyclopenta[l]phenanthren-2-ol revealed a near planar conformation for the fused imidazole moiety, suggesting the complex may be capable of binding to duplex DNA. Binding-induced changes in spectral properties, along

  抑制剂研究表明，羟基自由基主要负责DNA光裂解反应。初步研究表明，在黑暗中还发现1中的-OH官能团可水解pBR322的磷酸二酯键。
• Observation of supramolecular π–π dimerization of a dinuclear ruthenium complex by 1H NMR and ESMS
  作者：Eléna Ishow、André Gourdon

  DOI：10.1039/a805809a

  日期：——

  The dinuclear ruthenium complex of bisdipyrido[3,2-f:2′,3′-h]quinoxalo}[2,3-e:2′,3′-l]pyrene (bqpy) forms dimers in solution maintained only by π–π stacking of the bridging ligand, stable enough to be observed not only by 1H NMR spectroscopy but also by electrospray mass spectrometry at low accelerating cone voltage.

  双核钌络合物bisdipyrido[3,2-f:2′,3′-h]quinoxalo}[2,3-e:2′,3′-l]pyrene (bqpy) 在溶液中形成二聚体，这些二聚体仅通过桥接配体的π–π堆积维持，足够稳定，不仅可以通过1H NMR光谱法观察到，还可以通过低加速锥电压的电喷雾质谱法观察到。