pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline | 143174-44-1

• 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: pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline
• 英文别名: pyrido[2',3':5,6]pyrazino[2,3-f][1,10]phenanthroline；tripyridoquinoxaline；4,5,9,13,14-pentaaza-benzo[b]triphenylene；pyrido[2',3':5,6]pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile；dppp2；6,9,15,17,22-pentazapentacyclo[12.8.0.02,7.08,13.016,21]docosa-1(22),2(7),3,5,8(13),9,11,14,16(21),17,19-undecaene
• CAS: 143174-44-1
• 化学式: C₁₇H₉N₅
• 分子量: 283.292
• InChiKey: WSYPKJCYOBETJL-UHFFFAOYSA-N

物化性质

• 沸点：
  590.7±30.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• 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

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline 以 甲醇 为溶剂， 生成 [Cu(tripyridoquinoxaline)2(H2O)2](ClO4)2
  参考文献：
  名称：

  Cytotoxic copper(II) complex of tripyridoquinoxaline with DNA hydrolase activity

  摘要：

  A monomeric copper(II) complex, [Cu(tPq)(2)(H2O)(2)](ClO4)(2), (tpq = tripyridoquinoxaline), has been synthesized and characterized spectroscopically. This complex has been found to bind DNA intercalatively and the DNA binding constant, K-b, for this complex has been determined from absorption measurements and was found to be (5.7 +/- 0.3) x 10(3) M-1. This complex successfully promotes hydrolytic cleavage of plasmid DNA. producing single and double DNA strand breaks in the absence of any added cofactor. The amount of conversion of the supercoiled form of plasmid to the nicked circular form depends on the concentration of the copper complex as well as the duration of the incubation of the complex with DNA. The rate of conversion of SC to NC has been determined to be 2.65 x 10(-4) s(-1) at pH 7.2 in the presence of 80 mu M of the complex. This complex has also been shown to be cytotoxic towards A549 lung adenocarcinoma cells. This complex has been shown to bring about apoptosis of the cancerous A549 cell line. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.03.042
• 作为产物：
  描述：

  1,10-菲罗啉 在 硫酸 、 ammonium acetate 、 硝酸 、 溶剂黄146 、 potassium bromide 作用下， 反应 7.0h， 生成 pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline
  参考文献：
  名称：

  Insight into the intercalating ligands affecting the interactions of ruthenium(II) polypyridyl complexes with RNA poly(A)*poly(U)

  摘要：

  DOI：

  10.1016/j.poly.2023.116460

文献信息

• A Recyclable Solid Acid Catalyst Sulfated Titania for Easy Synthesis of Quinoxaline and Dipyridophenazine Derivatives under Microwave Irradiation
  作者：Balu Krishnakumar、Meenakshisundaram Swaminathan

  DOI：10.1246/bcsj.20110152

  日期：2011.11.15

  TiO2–SO42−, prepared by sol–gel method has been used for the synthesis of quinoxaline and dipyridophenizine derivatives under microwave irradiation. High-resolution transmission electron microscope (HR-TEM) and atomic force microscope (AFM) images reveal the corrosion of TiO2 particles by sulfuric acid, which causes an increase in the acidity of the catalyst. Sulfate loading by H2SO4 increases catalytic activity of TiO2. This catalyst gives an excellent yield with less reaction time and is an inexpensive, easily recyclable and efficient catalyst for this reaction.

  通过溶胶-凝胶法制备的TiO2–SO42−已用于在微波辐射下合成喹喔啉和二吡啶苯并嗪衍生物。高分辨率透射电子显微镜（HR-TEM）和原子力显微镜（AFM）图像揭示了硫酸对TiO2颗粒的腐蚀，从而导致催化剂酸性的增加。通过H2SO4进行的硫酸盐负载提高了TiO2的催化活性。该催化剂在较短的反应时间内提供了优异的产率，是一种价格低廉、易于回收和高效的催化剂。
• New organoruthenium compounds with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline: synthesis, characterization, cytotoxicity, and investigation of mechanism of action
  作者：Marijana Pavlović、Stefan Nikolić、Nevenka Gligorijević、Biljana Dojčinović、Sandra Aranđelović、Sanja Grgurić-Šipka、Siniša Radulović

  DOI：10.1007/s00775-019-01647-4

  日期：2019.3

  Three new ruthenium(II)-arene complexes with pyrido[2',3':5,6]pyrazino[2,3-f][1, 10]phenanthroline (ppf) of general formula: C1 ([(ƞ6-benzene)Ru(ppf)Cl]PF6, C2 ([(ƞ6-toluene)Ru(ppf)Cl]PF6) and C3 ([(ƞ6-p-cymene)Ru(ppf)Cl]PF6) have been synthesized. The structures of complexes were determined by elemental analysis, IR, ESI-MS, as well as with 1H and 13C NMR spectroscopy. Cytotoxic activity has been

  在A375细胞中进行的药物蓄积研究表明，与顺铂相比，C3进入细胞的能力较低，并且在细胞的细胞质和细胞膜/细胞器部分中平均分布。在A375细胞的3D模型中进行的研究表明，复合物C3和顺铂对多细胞肿瘤球体（MCTSs）生长的不同影响。尽管顺铂处理的MCTS的大小随时间减少，但用C3处理的MCTS继续增长。这种类型的钌（II）-芳烃配合物与顺铂在A375恶性黑色素瘤细胞中的结构组织和生物学活性的差异指出了它们的不同作用方式，是进行进一步生物学研究和优化潜在应用的必要性。
• Polyethylene glycol in water: A simple, efficient and green protocol for the synthesis of quinoxalines
  作者：HEMANT V CHAVAN、LAXMAN K ADSUL、BABASAHEB P BANDGAR

  DOI：10.1007/s12039-011-0081-8

  日期：2011.7

  quinoxaline derivatives has been efficiently synthesized in excellent yields under extremely mild conditions using PEG-600 and water. This inexpensive, non-toxic, eco-friendly and readily available system efficiently condensed several aromatic as well as aliphatic 1,2-diketones with aromatic and aliphatic 1,2-diamines to afford the products in excellent yield. Polyethylene glycol (PEG) can be recovered and

  使用PEG-600和水，已在极其温和的条件下以优异的收率高效合成了多种生物学上重要的喹喔啉衍生物。这种廉价，无毒，环保且易于获得的系统可将几种芳香族以及脂肪族1,2-二酮与芳香族和脂肪族1,2-二胺有效缩合，从而以优异的收率提供产品。聚乙二醇（PEG）可以回收再利用。 具有重要生物学意义的喹喔啉衍生物已使用PEG-600和水在极温和的条件下以高收率高效合成。
• Platinum(II) Complexes with Dipyridophenazine Ligands as Human Telomerase Inhibitors and Luminescent Probes for G-Quadruplex DNA
  作者：Dik-Lung Ma、Chi-Ming Che、Siu-Cheong Yan

  DOI：10.1021/ja806045x

  日期：2009.2.11

  A series of platinum(II) complexes containing dipyridophenazine (dppz) and C-deprotonated 2-phenylpyridine (N-CH) ligands were prepared and assayed for G-quadruplex DNA binding activities. [PtII(dppz-COOH)(N-C)]CF3SO3 (1; dppz-COOH = 11-carboxydipyrido[3,2-a:2',3'-c]phenazine) binds G-quadruplex DNA through an external end-stacking mode with a binding affinity of approximately 10(7) dm3 mol-1. G-quadruplex

  制备了一系列含有双吡啶并吩嗪 (dppz) 和 C-去质子化 2-苯基吡啶 (N-CH) 配体的铂 (II) 配合物，并测定了 G-四链体 DNA 结合活性。[PtII(dppz-COOH)(NC)]CF3SO3 (1; dppz-COOH = 11-carboxydipyrido[3,2-a:2',3'-c]phenazine) 通过外部末端堆叠结合 G-四链体 DNA模式的结合亲和力约为 10(7) dm3 mol-1。G-四链体 DNA 结合伴随着 lambdamax = 512 nm 处的光致发光强度增加高达 293 倍。使用生物素化引物延伸端粒酶测定，显示 1 是体外人端粒酶的有效抑制剂，telIC50 值为 760 nM。
• Highly Solvent Dependent Luminescence from [Ru(bpy)_<i>n</i>(dppp2)_3−<i>n</i>]²⁺ (<i>n</i> = 0−2)
  作者：Yujie Sun、Claudia Turro

  DOI：10.1021/ic100106b

  日期：2010.6.7

  photophysical properties of a series of ruthenium(II) complexes possessing the dppp2 (dppp2 = pyrido[2′,3′:5,6]pyrazino[2,3-f][1,10]phenanthroline) ligand, [Ru(bpy)n(dppp2)3−n]2+ (bpy = 2,2′-bipyridine; n = 0−3), were investigated. The dppp2-containing complexes possess a remarkable solvent dependence of the luminescence maximum, lifetime, and quantum yield. For example, the emission maximum of [Ru(bpy)2(dppp2)]2+

  一系列具有dppp2（dppp2 =吡啶并[2'，3'：5,6]吡嗪并[2,3- f ] [1,10]菲咯啉）配体[Ru（研究了bpy）n（dppp2）3- n ] 2+（bpy = 2,2'-联吡啶; n = 0-3）。含dppp2的配合物对最大发光量，寿命和量子产率具有显着的溶剂依赖性。例如，[Ru（bpy）2（dppp2）] 2+的最大发射蓝色从CH 3 CN中的752 nm变为CH 2 Cl 2中的653 nm，同时发光量子产率提高了19倍。电子结构计算，瞬态吸收光谱和电化学也可用于深入了解dppp2复合物的光物理性质。这些配合物发射的明显溶剂效应归因于环境中两个低位金属至配体电荷转移（MLCT）激发态的相对稳定性的变化，其中最低能量MLCT状态对环境更敏感。溶剂的极性比能量稍高的极性。瞬态吸收光谱法表明，最低能级MLCT状态的标识不会随溶剂的变化而变化，但是，其最大发射量和寿命受