1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol | 256525-25-4

• 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: 1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol
• CAS: 256525-25-4
• 化学式: C₂₃H₁₄N₄O
• 分子量: 362.39
• InChiKey: SXOSDLCRIWJVLW-UHFFFAOYSA-N

物化性质

• 沸点：
  717.3±70.0 °C(Predicted)
• 密度：
  1.463±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  74.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol 、 Eu(DBM)₃(H₂O)₂ 以 甲醇 为溶剂， 反应 4.0h， 以59%的产率得到[Eu(tris(dibenzoylmethanido))(2-(2-hydroxy-1-naphthyl)-1H-imidazo[4,5-f][1,10]phenanthroline)]
  参考文献：
  名称：

  萘基发色团官能化的咪唑并[4,5-f] [1,10]菲咯啉和二苯甲酰甲烷的三价镧系元素（III）配合物的合成，光物理和磁性研究。

  摘要：

  二苯甲酰甲烷（DBM）和2-（2-萘基）-1H的发光三价镧系元素（Ln（DBM）3（L1）]和[Ln（DBM）3（L2）]（Ln = Eu和Tb） -咪唑并[4,5-f] [1,10]菲咯啉（L1）和2-（2-羟基-1-萘基）-1H-咪唑并[4,5-f] [1,10]菲咯啉（L2）被报道。萘基发色团官能化的咪唑并菲咯啉配体L1和L2通过单晶X射线衍射进行结构表征：（L1），a = 14.933（4）Å，b = 7.4965（13）Å，c = 15.999（4）Å，α = γ= 90°，β = 102.670（7）°，V = 1747.4（6）3，Ž = 4，单斜，P21 / C和（L2），一个= 7.8555（11）埃，b = 26.216（4） ，ç = 10.0748（17）A，α = γ = 90°，β = 96.799（7）°，V = 2060.2（6）3，ž = 4，单斜，P21

  DOI：

  10.1039/c7dt01133d
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 、 2-羟基-1-萘甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 反应 3.0h， 以55%的产率得到1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol
  参考文献：
  名称：

  萘咪唑并菲咯啉（HNAIP）配体及其[Ir（ppy）2（HNAIP）] Cl和[Rh（ppy）2（HNAIP）] Cl配合物的生物活性和光催化性能。

  摘要：

  合成的2-（羟基-1-萘基）咪唑-[4,5-f] [1,10]菲咯啉（HNAIP）配体及其新铱（[Ir（ppy）2（HNAIP）] Cl）和铑（ [Rh（ppy）2（HNAIP）] Cl）复合物为ppy = 2-phenylpiridinate，在SW480（结肠腺癌）和A549（上皮肺腺癌）细胞中显示出细胞毒性作用。它们在测试的细胞系中均具有细胞毒性。HNAIP和[Rh（ppy）2（HNAIP）] +具有最大的细胞毒性，而[Ir（ppy）2（HNAIP）] +对A549细胞的细胞毒性微不足道，对SW480的活性中等。研究了这三种化合物与牛血清白蛋白（BSA），1-谷胱甘肽还原（GSH），烟酰胺腺嘌呤二核苷酸（NADH）和DNA的相互作用，以解释在细胞毒性方面的差异。他们都无法与BSA互动，因此排除了由于血浆蛋白相互作用而引起的生物利用度，将其作为生物活性中可能的差异化因素。相比之下，已观

  DOI：

  10.1016/j.jinorgbio.2019.110885

文献信息

• Synthesis and structural characterization of a novel 2D supramolecular lead coordination polymer with phenanthroline derivate and adipic acid
  作者：Yu Song、Yu Yan、Hua Zhang、Xiuyan Wang

  DOI：10.1515/mgmc-2021-0025

  日期：2021.1.1

  A new metal-organic coordination polymer, [Pb(L)(adip)_0.5] (1) was synthesized under hydrothermal conditions by using 1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol (HL) and adipic acid (H₂adip). The complex 1 was characterized by diffraction and elemental analyses. In complex 1, the binuclear [Pb₂L₂] units were formed by the OH-deprotonation bridging neighboring Pb(II) atoms, and the adipate linked the binuclear [Pb₂L₂] units to form a symmetric one-dimensional chain. The 1D chain was further extended to the 2D supramolecular layer structure through π-π interactions between the L ligands.

  在水热条件下，使用1-(1H-咪唑[4,5-f][1,10]菲啰啉-2-基)萘-2-醇（HL）和己二酸（H2adip）合成了一种新的金属有机配位聚合物[Pb(L)(adip)0.5]（1）。复合物1通过衍射和元素分析进行了表征。在复合物1中，双核[Pb2L2]单元通过羟基去质子桥接相邻的Pb（II）原子形成，并且己二酸连接双核[Pb2L2]单元形成对称的一维链。通过L配体之间的π-π相互作用，1D链进一步扩展为2D超分子层结构。

• Synthesis and Crystal Structure of a New Pb(II) Coordination Polymer Constructed by a 1,10-Phenanthroline Derivative and a Flexible Dicarboxylate
  作者：Xiu-Yan Wang、Jia Guo、Hui-Lian Wang、Qing-Wei Wang

  DOI：10.1515/znb-2011-0614

  日期：2011.6.1

  Z = 4. The Pb(II) atoms are bridged by the flexible trans-1,4-chdc ligands to form a zigzag chain. The ligands L are located on both sides of the zigzag chains, where π-π interactions among neighboring zigzag chains give rise to a two-dimensional supramolecular network. In addition, O-H···O and N-H···O hydrogen bonding interactions further stabilize the supramolecular network structure of 1. Graphical

  新型配位聚合物 [Pb(L)(trans-1,4-chdc)] 1 (L = 1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)-naphthalen -2-ol 和 trans-1,4-H2chdc = trans-1,4-环己烷二甲酸），已通过水热合成并通过元素分析、红外光谱和单晶 X 射线衍射表征。晶体数据：C31H24N4O5Pb，单斜晶系，空间群 P21/c，a = 13.579(2)，b = 9.7831(15)，c = 19.958(3) Å，β = 105.058(2)°，V = 2560.3(7) , Z = 4. Pb(II) 原子被灵活的 trans-1,4-chdc 配体桥接形成锯齿形链。配体 L 位于锯齿形链的两侧，相邻锯齿形链之间的 π-π 相互作用产生二维超分子网络。此外，OH···O和NH···O氢键相互作用进一步稳定了1的超分子网络结构。
• Synthesis and crystal structure of one new cadmium coordination polymer constructed by phenanthroline derivate and 1,4-naphthalenedicarboxylic acid
  作者：Na Xu、Minghe Cui、Yueyue Zhang、Limin Chang、Zhiguo Kong、Zhanlin Xu

  DOI：10.1515/mgmc-2022-0005

  日期：2022.6.10

  A cadmium coordination polymer, [Cd(1,4-NDC)(L)] _n (1), has been hydrothermally synthesized by using 1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol (L) and 1,4-naphthalenedicarboxylic acid (1,4-H₂NDC). The complex 1 was characterized by diffraction and elemental analyses. In complex 1, the cadmium ion is distorted octahedral coordinated linking the deprotonated 1,4-NDC anion to form a two-dimensional (2D) layer, and the 2D layer are associated into 3D supramolecular structure via the strong π–π stacking interactions from the conjugated L ligands. In addition, thermogravimetry, powder X-ray diffraction, and the solid-state photoluminescent properties of complex 1 were also studied.

  使用1-(1H-咪唑[4,5-f][1,10]菲啰啉-2-基)萘-2-醇(L)和1,4-萘二羧酸(1,4-H2NDC)通过水热合成了一种镉配位聚合物，[Cd(1,4-NDC)(L)]_n (1)。通过衍射和元素分析对复合物1进行了表征。在复合物1中，镉离子经变形八面体配位连接去质子化的1,4-NDC阴离子形成二维层，并通过共轭L配体的强π-π堆积相互作用将二维层结合成三维超分子结构。此外，还研究了复合物1的热重分析、粉末X射线衍射和固态光致发光性质。

• A new cadmium(ii) coordination polymer with 1,4-cyclohexanedicarboxylate acid and phenanthroline derivate: Synthesis and crystal structure
  作者：Beihao Su、Yihan Shi、Xuehan Peng、Zhiguo Kong、Limin Chang

  DOI：10.1515/mgmc-2022-0020

  日期：2022.9.24

  A new Cd(ii) coordination polymers, formulated as [Cd(1,4-chdc)(L)] _n (1) (L = 1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol ligands and 1,4-H₂chdc = 1,4-cyclohexanedicarboxylate acid), were successfully synthesized by using L ligand and 1,4-H₂chdc acid under hydrothermal conditions and characterized by single crystal X-ray elemental analyses, diffraction, and IR spectroscopy. Each Cd(ii) atom is a distorted pentagonal bipyramidal geometry connecting the deprotonated 1,4-chdc anion to form a 2D layer, and a 2D layer is formed into a 3D supramolecular structure by the π–π stacking interactions between neighboring layers.

  摘要 一种新的镉(ii)配位聚合物，配位形式为[Cd(1,4-chdc)(L)]。 n (1) （L = 1-(1H-咪唑并[4,5-f][1,10]菲罗啉-2-基)萘-2-醇配体和 1,4-H2chdc = 1,4-Cyclohexanedarboxylate acid），并通过单晶 X 射线元素分析、衍射和红外光谱进行了表征。每个镉(ii)原子都是畸变的五角双锥几何形状，连接去质子化的 1,4-chdc 阴离子形成二维层，二维层通过相邻层之间的 π-π 堆垛相互作用形成三维超分子结构。
• Effect of intramolecular hydrogen-bond on the DNA-binding and photocleavage properties of polypyridyl cobalt(III) complexes
  作者：Qian-Ling Zhang、Jin-Gang Liu、Jian-Zhong Liu、Hong Li、Yi Yang、Hong Xu、Hui Chao、Liang-Nian Ji

  DOI：10.1016/s0020-1693(02)00923-4

  日期：2002.11

  Two polypyridyl cobalt(III) complexes containing intramolecular hydrogen-bond [Co(phen)(2)HPIP](3+) (HPIP = 2-(2-hydroxyphenyl)imidazo[4,5-f][1,10]phenanthroline) and [Co(phen)(2)HNAIP](3+) (HNAIP = 2-(2-hydroxy-1-naphthyl)imidazo[4,5-f][1,10]phenanthroline) have been synthesized and characterized by UV-Vis, EA and MS spectra. Binding of both complexes with calf thymus DNA has been investigated by cyclic voltammetry, absorption spectroscopy, luminescence titration, viscosity measurements and DNA cleavage assay. The results suggested that the complex [Co(phen)(2)HPIP](3+) bound to CT DNA by intercalation via HPIP into the base pairs of DNA, while [Co(phen)(2)HNAIP](3+) bound with DNA by partial intercalating the ligand HNAIP. In addition, both complexes have been found to promote the single-stranded cleavage of plasmid pBR 322 DNA upon irradiation, and [Co(phen)(2)HPIP](3+) exhibited the higher cleaving efficiency. (C) 2002 Published by Elsevier Science B.V.