4-bromo-2-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol | 1420904-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-bromo-2-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol
• 英文别名: 4-Bromo-2-(1h-imidazo[4,5-f][1,10]phenanthrolin2-yl)phenol
• CAS: 1420904-53-5
• 化学式: C₁₉H₁₁BrN₄O
• 分子量: 391.227
• InChiKey: SJHCTHAKBUZNMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• 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：

  copper(II) choride dihydrate 、 4-bromo-2-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以52%的产率得到
  参考文献：
  名称：

  Gomleksiz, Mesut; Alkan, Cihan; Erdem, Belgin, South African Journal of Chemistry, 2013, vol. 66, p. 107 - 112

  摘要：

  DOI：
• 作为产物：
  描述：

  5,6-二氨基-1,10-邻菲罗啉 、 5-溴水杨醛 在 双氧水 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以73%的产率得到4-bromo-2-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol
  参考文献：
  名称：

  Synthesis, structures and aggregation-induced emissive properties of copper(I) complexes with 1H-imidazo[4,5-f][1,10]phenanthroline derivative and diphosphine as ligands

  摘要：

  Reaction of 4-bromo-2-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol (BIPP), chelating diphosphine ligands and [Cu(MeCN)(4)]ClO4 afforded five mononuclear [Cu(BIPP)(PP)]ClO4 (PP = dppe, 1; dppp, 2; bdpp, 3; POP, 4; xantphos, 5) complexes with good phosphorescent emission in the solid state. All the complexes are characterized by elemental analyses, electrospray Ionization mass spectra, H-1 and P-31 NMR spectra and X-ray single crystallography. The photoluminescence quantum yields of complexes 1-5 are from less than 0.010 to 0.262 in the solid state under air atmosphere, which increase with the increasing rigidity of diphosphine ligands and the increasing strength of intermolecular and intramolecular pi center dot center dot center dot pi interactions. The aggregation-induced emission of complexes 4 and 5 at room temperature was investigated. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.05.019

文献信息

• Luminescent agostic Cu(I) complexes containing both trigonal planar and tetrahedral coordination modes
  作者：Miao-Miao Huang、Ya-Meng Guo、Ying Shi、Ling Zhao、Yan-Wen Niu、Yanhui Shi、Xiu-Ling Li

  DOI：10.1016/j.ica.2016.12.017

  日期：2017.3

  rigid chelating diphosphine ligand 9,9-dimethyl-4,5-bis(diphenylphosphino)-9H-xanthene (xantphos) under alkaline conditions in different ratios afforded a series of luminescent binuclear [Cu2(L–H)(xantphos)2]ClO4 (L = L1, 1a; L2, 2a; L3, 3a) and trinuclear [Cu3(L–2H)(xantphos)3]ClO4 (L = L1, 1b; L2, 2b; L3, 3b) complexes. Both trigonal planar and tetrahedral coordination modes of Cu(I) centers were observed

  [Cu（MeCN）4] ClO4与1H-咪唑并[4,5-f] [1,10]菲咯啉衍生物（L1，L2和L3）和笨重的刚性螯合二膦配体9,9-二甲基-C反应4,5-双（二苯基膦基）-9H-x吨（黄磷）在碱性条件下以不同比例提供一系列的发光双核[Cu2（L–H）（xantphos）2] （L = L1，1a; L2，2a ; L3，3a）和三核[Cu3（L-2H）（xantphos）3] （L = L1，1b; L2，2b; L3，3b）络合物。对于配合物1a和1b，都观察到了Cu（I）中心的三角形平面和四面体配位模式，并且它们对于三角形平面Cu（I）的中心表现出明显的CH⋯Cu错位或反位相互作用。讨论了31P NMR，电子吸收和发射光谱。在室温下，所有配合物在固态和溶液中均显示弱发光。
• GSH-resistant and highly cytoselective ruthenium(<scp>ii</scp>)-<i>p</i>-cymene-(imidazo[4,5-<i>f</i>][1,10]phenanthrolin-2-yl)phenol complexes as potential anticancer agents
  作者：Binoy Kar、Utpal Das、Sourav De、Sudhindra Pete、Ajay Sharma S、Nilmadhab Roy、Ashok Kumar S. K.、Debashis Panda、Priyankar Paira

  DOI：10.1039/d1dt01604k

  日期：——

  Ruthenium(ii)-p-cymene-imidazophenanthroline complexes were developed as highly cytoselective and GSH-resistant anticancer agents against HeLa and Caco-2 cell lines.

  钌（II）-p-环戊二甲基苯基咪唑菲啉配合物被开发为针对HeLa和Caco-2细胞系高度细胞选择性和对GSH抗性的抗癌药物。
• Copper(<scp>i</scp>) ionic complexes based on imidazo[4,5-<i>f</i>][1,10]phenanthrolin diimine chelating ligands: crystal structures, and photo- and electroluminescence properties
  作者：Anton V. Rozhkov、Svetlana N. Eliseeva、Sergey V. Baykov、Lev E. Zelenkov、Dmitry O. Goriachiy、Ilya V. Taydakov

  DOI：10.1039/c9nj05109k

  日期：——

  Four new ionic diimine Cu(I) complexes with general formula [Cu(POP)(NN)]BF4 have been synthesized by convenient methods from readily available starting materials. All the complexes were characterized by a range of spectroscopic, electrochemical, and computational techniques and, in the cases of 1, 2, and 3, by single crystal X-ray diffraction. The complexes are emissive in the solid state at ambient

  通过方便的方法，从容易获得的起始原料中合成了四种通式为[Cu（POP）（NN）] BF 4的新型离子二亚胺Cu（I）配合物。由一系列光谱学，电化学，和计算技术的所有的复合物，其特征在于，在的情况下1，2，和3，通过单晶X射线衍射。该复合物在环境温度下以固态发射，并且发射最大值位于橙色范围内。此外，已经在溶液处理的设备中证明了这些配合物在有机发光二极管（OLED）中的适用性。
• Iridium(<scp>iii</scp>)–Cp*-(imidazo[4,5-<i>f</i>][1,10]phenanthrolin-2-yl)phenol analogues as hypoxia active, GSH-resistant cancer cytoselective and mitochondria-targeting cancer stem cell therapeutic agents
  作者：Binoy Kar、Shanooja Shanavas、Apoorva H. Nagendra、Utpal Das、Nilmadhab Roy、Sudhindra Pete、Ajay Sharma S、Sourav De、Ashok Kumar S K、Seshu Vardhan、Suban K. Sahoo、Debashis Panda、Sudheer Shenoy、Bipasha Bose、Priyankar Paira

  DOI：10.1039/d2dt00168c

  日期：——

  exhibited highly cytotoxic effects on the HCT-116 CSC cell line. This complex was localized in the mitochondria and subsequent mitochondrial dysfunction was observed via MMP alteration and ROS generation on colorectal cancer stem cells. Cell cycle analysis also established the potential of this complex in mediating G2/M phase cell cycle arrest.

  在此，我们通过方便的合成方法引入了一系列铱( III )-Cp*-(咪唑并[4,5 - f ][1,10]菲咯啉-2-基)苯酚配合物，它们作为缺氧活性和谷胱甘肽抗性抗癌金属治疗剂。在合成的复合物中，[Ir III (Cp*)(L5)(Cl)](PF 6 ) ( IrL5 ) 复合物在HeLa和Caco-2细胞中表现出最好的细胞选择性、GSH抗性和缺氧效果。IrL5还表现出对 HCT-116 CSC 细胞系的高度细胞毒性作用。该复合物位于线粒体中，随后通过以下方式观察到线粒体功能障碍结直肠癌干细胞的 MMP 改变和 ROS 生成。细胞周期分析还确定了这种复合物在介导 G2/M 期细胞周期停滞方面的潜力。
• Synthesis, Structure, and Luminescence Properties of Boron Complex with 4-Bromo-2-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenoxide Ligand
  作者：A. V. Rozhkov、A. S. Novikov

  DOI：10.1134/s1070363219110148

  日期：2019.11

  A boron complex with 4-bromo-2-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenoxide ligand has been synthesized, and its photoluminescence properties in solution and in the solid phase have been examined. The structure of the complex has been determined by X-ray analysis. Non-classical intermolecular interaction (halogen bond) between the bromine and fluorine atoms has been detected in the crystal structure of the complex.