2-(imidazol-4-yl)-1H-imidazo[4,5-f][1,10]phenanthroline | 1227962-87-9

• 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: 2-(imidazol-4-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-(1H-imidazol-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
• CAS: 1227962-87-9
• 化学式: C₁₆H₁₀N₆
• 分子量: 286.296
• InChiKey: YOAHIXLWIMTSDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 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：
  83.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 、 2-(imidazol-4-yl)-1H-imidazo[4,5-f][1,10]phenanthroline 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  A Semi‐Automated, High‐Throughput Approach for the Synthesis and Identification of Highly Photo‐Cytotoxic Iridium Complexes

  摘要：

  The discovery of new compounds with pharmacological properties is usually a lengthy, laborious and expensive process. Thus, there is increasing interest in developing workflows that allow for the rapid synthesis and evaluation of libraries of compounds with the aim of identifying leads for further drug development. Herein, we apply combinatorial synthesis to build a library of 90 iridium(III) complexes (81 of which are new) over two synthesise‐and‐test cycles, with the aim of identifying potential agents for photodynamic therapy. We demonstrate the power of this approach by identifying highly active complexes that are well‐tolerated in the dark but display very low nM phototoxicity against cancer cells. To build a detailed structure–activity relationship for this class of compounds we have used density functional theory (DFT) calculations to determine some key electronic parameters and study correlations with the experimental data. Finally, we present an optimised semi‐automated synthesise‐and‐test protocol to obtain multiplex data within 72 hours.

  DOI：

  10.1002/anie.202401808
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 、 4-咪唑甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 反应 3.0h， 以63%的产率得到2-(imidazol-4-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  新合成的杂合铂（II）复合物[Pt（bpy）（iip）] 2+和[Pt（bpy）（miip）] 2+的DNA研究

  摘要：

  [Pt（bpy）（iip）] [PF 6）2（1）和[Pt（bpy）（miip）]（PF 6）2 ·2H 2 O（2）（bpy是2,2'-联吡啶; iip是2-（咪唑-4-基）-1 H-咪唑[4,5- f ] [1,10]菲咯啉; miip是2-（1-甲基咪唑-已合成并通过CHN分析，电喷雾电离和MALDI-TOF质谱法对2-yl）-1 H-咪唑并[4,5- f ] [1，10 ]菲咯啉进行了全面表征，1H NMR，FT-IR（ATR）和UV-Vis分光光度计。研究了该复合物的细胞毒性，抑制DNA转录的能力和DNAse活性。还已经通过光谱方法，循环伏安法和粘度测量研究了两种复合物的DNA结合行为。两种复合物均显示出细胞毒特性，其中2种比1种具有更高的细胞毒性。随着两种复合物浓度的增加，DNA转录被抑制。发现复合物2是比1更好的抑制剂。在复合物的DNA酶谱中可以看到相同的模式。此外，发现有2种以低于1的浓度促进pBR322

  DOI：

  10.1007/s00775-015-1317-8

文献信息

• DNA studies of newly synthesized heteroleptic platinum(II) complexes [Pt(bpy)(iip)]2+ and [Pt(bpy)(miip)]2+
  作者：Burak Coban、Ishak Ozel Tekin、Abdurrahman Sengul、Ufuk Yildiz、Izzet Kocak、Nergis Sevinc

  DOI：10.1007/s00775-015-1317-8

  日期：2016.4

  transcription and DNAse activity of the complexes were studied. The DNA-binding behaviors of both complexes have also been studied by spectroscopic methods, cyclic voltammetry and viscosity measurements. Both complexes showed cytotoxic properties and 2 was more cytotoxic than 1. DNA transcription was inhibited upon increasing concentrations of both complexes. The complex 2 was found to be a better inhibitor

  [Pt（bpy）（iip）] [PF 6）2（1）和[Pt（bpy）（miip）]（PF 6）2 ·2H 2 O（2）（bpy是2,2'-联吡啶; iip是2-（咪唑-4-基）-1 H-咪唑[4,5- f ] [1,10]菲咯啉; miip是2-（1-甲基咪唑-已合成并通过CHN分析，电喷雾电离和MALDI-TOF质谱法对2-yl）-1 H-咪唑并[4,5- f ] [1，10 ]菲咯啉进行了全面表征，1H NMR，FT-IR（ATR）和UV-Vis分光光度计。研究了该复合物的细胞毒性，抑制DNA转录的能力和DNAse活性。还已经通过光谱方法，循环伏安法和粘度测量研究了两种复合物的DNA结合行为。两种复合物均显示出细胞毒特性，其中2种比1种具有更高的细胞毒性。随着两种复合物浓度的增加，DNA转录被抑制。发现复合物2是比1更好的抑制剂。在复合物的DNA酶谱中可以看到相同的模式。此外，发现有2种以低于1的浓度促进pBR322
• A Semi‐Automated, High‐Throughput Approach for the Synthesis and Identification of Highly Photo‐Cytotoxic Iridium Complexes
  作者：Timothy Kench、Arielle Rahardjo、Gianmarco G. Terrones、Adinarayana Bellamkonda、Thomas E. Maher、Marko Storch、Heather J. Kulik、Ramon Vilar

  DOI：10.1002/anie.202401808

  日期：2024.4.24

  The discovery of new compounds with pharmacological properties is usually a lengthy, laborious and expensive process. Thus, there is increasing interest in developing workflows that allow for the rapid synthesis and evaluation of libraries of compounds with the aim of identifying leads for further drug development. Herein, we apply combinatorial synthesis to build a library of 90 iridium(III) complexes (81 of which are new) over two synthesise‐and‐test cycles, with the aim of identifying potential agents for photodynamic therapy. We demonstrate the power of this approach by identifying highly active complexes that are well‐tolerated in the dark but display very low nM phototoxicity against cancer cells. To build a detailed structure–activity relationship for this class of compounds we have used density functional theory (DFT) calculations to determine some key electronic parameters and study correlations with the experimental data. Finally, we present an optimised semi‐automated synthesise‐and‐test protocol to obtain multiplex data within 72 hours.