pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarboxylic acid | 573719-87-6

• 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: pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarboxylic acid
• 英文别名: 2,3-Dicarboxypyrazino[2,3-f][1,10]phenanthroline；(2,3-f)pyrazino(1,10)phenanthroline-2,3-dicarboxylic acid；2,3-pyrazino[1,10]phenanthroline-2,3-dicarboxylic acid；1,4,8,9-tetraazatriphenylene-2,3-dicarboxylic acid；H2PPDA
• CAS: 573719-87-6
• 化学式: C₁₆H₈N₄O₄
• 分子量: 320.264
• InChiKey: MBKYRTQDCNGSCW-UHFFFAOYSA-N

物化性质

• 熔点：
  >350 °C
• 沸点：
  638.7±55.0 °C(Predicted)
• 密度：
  1.687±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarboxylic acid 、 silver(I) acetate 在 邻苯二胺 作用下， 以 乙醇 为溶剂， 以66%的产率得到[Ag(Hppdb)(pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarboxylic acid)]n
  参考文献：
  名称：

  吡嗪并[2,3-f][1,10]菲咯啉-2,3-二羧酸银配合 物、制备方法及其应用

  摘要：

  本发明涉及一种吡嗪并[2,3-f][1,10]菲咯啉-2.3-二羧酸银配合物及其制备方法应用，配合物化学式为：[Ag(Hppdb)(H2ppdb)]n，其中H2ppdb为吡嗪并[2,3-f][1,10]菲咯啉-2.3-二羧酸配体。在水热的条件下，将吡嗪并[2,3-f][1,10]菲咯啉-2.3-二羧酸、btp、碱和金属银盐溶于水中，并封入反应釜中，以每小时10℃的速率加热至120~160℃，维持3天，然后自然条件下降至室温，得到目标产物。可将该材料应用于荧光材料上，该材料稳定性好，合成简单，操作方便，产率高和可重现性好等优点，获得的晶态材料可在荧光材料领域广泛应用。

  公开号：

  CN104230964B
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 以 乙醇 、 硫酸 为溶剂， 反应 10.0h， 生成 pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarboxylic acid
  参考文献：
  名称：

  Evaluation of the potential effectiveness of ruthenium(II) complexes with 2,3-disubtituted pyrazino[2,3-f][1,10]phenanthroline anchors, R2ppl (R=CN, COOH, COOEt, OH) as sensitizers for solar cells

  摘要：

  The ligands of type pyrazino[2,34][1,10]phenanthroline, R(2)ppl, with R = CN, COOH, COOEt or OH, were synthesized and used as precursors for obtaining the corresponding series of complexes of type [Ru(dmbpy)(2)R(2)ppl](PF6)(2), where dmbpy is 4,4'-dimethyl-2,2'-bipyridine. The compounds were prepared, characterized, and studied by theoretical DFT calculations in order to evaluate their potentiality as dyes in photoelectrochemical cells.The electron acceptor capacity of the R(2)ppl ligands was evaluated by analyzing parameters such as electrophilicity and charge distribution on the reduced ligand. Additionally, the R substituents on R(2)ppl were evaluated as anchoring groups, by variables such as highest spin occupied molecular orbital (HSOMO). Finally, the I-T parameter was defined and calculated. This is related to the amount of energy that can be delivered to TiO2 from the acceptor anchoring ligand in the thexi state. According to this parameter, the [Ru(dmbpy)(2)(COOH)(2)ppl](PF6)(2) complex is predicted to have the best response, among the compounds of the series, when used as dye in a solar cell. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.12.003

文献信息

• Synthesis, Structures, and Properties of Two Novel Supramolecular Architectures Constructed from [2,3-f]Pyrazino[1,10]phenanthroline-2,3-dicarboxylic Acid
  作者：Xiao-Ning Zhang、Dong-Sheng Li、Ji-Jiang Wang、Jun Zhao、Cai-Xia Meng、Ya-Pan Wu、Yao-Yu Wang

  DOI：10.1002/zaac.200900223

  日期：2009.12

  Two new compounds, [Ag(Hppdb)]n (1) and [Ag2(Hppdb)2(bpe)]·5.5H2O}n(2) [H2ppdb = [2,3-f]pyrazino[1,10]phenanthroline-2,3-dicarboxylic acid, bpe = trans-1,2-bis(4-pyridyl)ethylene], were synthesized and characterized. In 1, Hppdb– ions link AgI cations to form an infinite 1D [–Ag–(Hppdb)–Ag–]n chain, furthermore, the dimensionality is extended to 2D layers through synergistic π–π stacking, hydrogen-bonding

  两种新化合物，[Ag(Hppdb)]n (1) 和 [Ag2(Hppdb)2(bpe)]·5.5H2O}n(2) [H2ppdb = [2,3-f]pyrazino[1,10]菲咯啉-2,3-二羧酸，bpe = trans-1,2-bis(4-pyridyl)ethylene]，合成并表征。在1中，Hppdb–离子连接AgI阳离子形成无限的一维[–Ag–(Hppdb)–Ag–]n链，此外，通过协同π–π堆积、氢键和弱Ag将维数扩展到二维层···O 互动。相应地，2中的二聚体[(Ag)(Hppdb)]2亚基通过bpe配体连接产生环链状的一维链基序，进一步通过R22(18)C-H···O连接氢键环以提供有趣的对角/对角倾斜链 2D + 2D 3D 超分子结构。此外，
• Synthesis, structure, photoluminescence and theoretical calculations on a novel tetranuclear Cd(II) complex based on (2,3-f)-pyrazino(1,10)phenanthroline-2,3-dicarboxylic acid
  作者：Hui-Fen Chen、Ming-Jian Zhang、Ming-Sheng Wang、Wen-Bin Yang、Xiang-Guang Guo、Can-Zhong Lu

  DOI：10.1016/j.inoche.2012.06.022

  日期：2012.9

  novel tetranuclear cadmium complex Cd2[(CH3)2PPDA]2(CH3OH)Cl4}2 (1) [(CH3)2PPDA = dimethyl esterification of H2PPDA], was prepared from CdCl2·2.5H2O with (2,3-f)-pyrazino(1,10)phenanthroline-2,3-dicarboxylic acid (H2PPDA) by solvothermal reaction in methanol, and characterized by single-crystal X-ray diffraction analysis, optical diffuse reflectance and photoluminescence. In 1, cadmium ions are bridged

  摘要 以 CdCl2·2.5H2O 与 (2,3-f )-吡嗪基 (1,10) 菲咯啉-2,3-二羧酸 (H2PPDA) 在甲醇中通过溶剂热反应制备，并通过单晶 X 射线衍射分析、光学漫反射和光致发光表征。在图 1 中，镉离子被 Cl− 离子桥接成四核寡聚链，通过分子间 CH⋯Cl、OH⋯Cl 和 CH⋯O 氢键进一步连接成 3D 超分子网络。化合物 1 在可见光激发下在可见光区显示出寿命值为 ~ 5.88 ns 的荧光，
• Two uranyl heterocyclic carboxyl compounds with fluorescent properties as high sensitivity and selectivity optical detectors for nitroaromatics
  作者：Shuang Li、Li Xian Sun、Jue Chen Ni、Zhan Shi、Yong Heng Xing、Di Shang、Feng Ying Bai

  DOI：10.1039/c6nj03933b

  日期：——

  detected. The experimental results suggest a high selective quenching of initial fluorescence intensity in the presence of nitroaromatic compounds. And by calculating the quenching constants of the nitroaromatics using the SV equation (I0/I) = KSV[A] + 1, we can see the KSV values of the quencher 2,4,6-trinitrophenol are both largest for the two compounds, and the values are 1.6 × 106 and 8.5 × 105 for

  基于不同的杂环羧基，合成了两种化合物UO 2（C 16 H 7 N 4 O 4）2 ·2H 2 O（1）和UO 2（C 20 H 12 N 5 O 2）2（2）。配体2,3-吡嗪并[1,10]菲咯啉-2,3-二羧酸（H 2 L 1）和2,6-双（2-吡嗪基）吡啶-4-苯甲酸（HL 2）。通过元素分析，红外光谱，PXRD，热重分析和紫外可见光谱对这两种化合物进行了表征。单晶X射线衍射分析表明，化合物1和2均表现出2D片状结构。此外，化合物的荧光淬灭性质的研究1和2表明，发光强度为既减小1和2是特别明显与硝基芳香化合物浓度的增加，即使硝基芳族化合物是在非常低的浓度（对于1为15 ppm时，为2它是20 ppm），也可以检测到。实验结果表明在硝基芳族化合物存在下，初始荧光强度的高选择性猝灭。通过使用SV方程（I 0 / I）= K SV [A] + 1计算硝基芳香族化合物的淬灭常数，我们可以看到，淬灭剂2
• Novel mononuclear Pt2+ and Pd2+ complexes containing (2,3-f)pyrazino(1,10)phenanthroline-2,3-dicarboxylic acid as a multi-donor ligand. Synthesis, structure, interaction with DNA, in vitro cytotoxicity, and apoptosis
  作者：Ya-guang Sun、Yi-ning Sun、Li-xin You、Yi-nan Liu、Fu Ding、Bao-yi Ren、Gang Xiong、Valerian Dragutan、Ileana Dragutan

  DOI：10.1016/j.jinorgbio.2016.09.008

  日期：2016.11

  New cytotoxic, mononuclear Pt and Pd coordination complexes featuring the planar, multi-donor ligand (2,3-f)pyrazino(1,10)phenanthroline-2,3-dicarboxylic acid (H2PPDA) have been synthesized under hydrothermal conditions (in water, at high temperature and pressure) and fully characterized. The complexes were proven to be isostructural by applying the single-crystal X-ray diffraction technique. UV–Vis

  在水热条件下已经合成了具有平面，多供体配体（2,3- f）吡嗪并（1,10）菲咯啉-2,3-二羧酸（H 2 PPDA）的新型细胞毒性单核Pt和Pd配位配合物（在水中，高温高压下）并具有充分的特征。通过应用单晶X射线衍射技术，证明该配合物是同构的。UV-Vis和荧光光谱法研究了它们与鱼精DNA的相互作用，显示了相当大的结合能力，而凝胶电泳提供了支持pBR322质粒DNA裂解的证据。新合成的复合物在体外表现出显着的意义 对两种不同的人类癌细胞系KB和JEKO细胞具有细胞毒活性，细胞死亡主要是由凋亡引起的。
• Two new Ag(I)-based compounds: luminescence and enhancing acupuncture treatment activity on ovarian cancer
  作者：Meng-Jie Chen、Yao-Hua Chen、Xue-Lian Hui

  DOI：10.1007/s11696-022-02251-8

  日期：2022.9

  This contribution reported two fresh Ag(I)-based compounds, as known as [Ag2(L1)(H2O)]n (1) and [Ag2(L2)(NO3)2]n (2) (H2L1 = 1,4,8,9-tetraazatriphenylene-2,3-dicarboxylic acid, L2 = tris(pyridin-2-yl)-1,3,5-triazine), that were formed in hydrothermal environments and further structurally researched by the aid of powder X-ray diffraction, elemental analysis, X-ray single crystal diffraction and thermogravimetric

  该贡献报告了两种新的基于 Ag(I) 的化合物，称为 [Ag 2 (L1)(H 2 O)] n (1) 和 [Ag 2 (L2)(NO 3 ) 2 ] n (2) ( H 2L1 = 1,4,8,9-tetraazatriphenylene-2,3-dicarboxy acid, L2 = tris(pyridin-2-yl)-1,3,5-triazine)，在热液环境中形成，并通过借助粉末X射线衍射、元素分析、X射线单晶衍射和热重分析。在适当的激发波长下，1和2的固体粉末是发光的。研究了它们联合针灸治疗卵巢癌的作用，同时研究了相关原理。首次完成细胞计数试剂盒8（CCK-8）测定，评价了新鲜化合物对癌细胞的抑制作用。然后，还评估了卵巢癌细胞中血管内皮生长因子 (VEGF) 信号通路的活性。