2-(1H-benzimidazol-2yl)-1H-imidazo[4,5-F][1,10]phenanthroline | 1444124-50-8

• 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-(1H-benzimidazol-2yl)-1H-imidazo[4,5-F][1,10]phenanthroline
• 英文别名: 2-(1H-benzo[d]imidazol-2-yl)-1H-imidazo[4,5-f][1,10]phenanthroline；2-(1H-benzimidazol-2-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
• CAS: 1444124-50-8
• 化学式: C₂₀H₁₂N₆
• 分子量: 336.355
• InChiKey: KWLDVBFKTHSKRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 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：
  83.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 顺-双(2,2-二吡啶)二氯化钌(II) 水合物 、 2-(1H-benzimidazol-2yl)-1H-imidazo[4,5-F][1,10]phenanthroline 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 [Ru(2,2'-bipyridyl)2(2-(1H-imidazol-2yl)-1H-imidazo[4,5-F][1,10]phenanthroline )](PF6)2
  参考文献：
  名称：

  Unusual solvent dependent emission property of two new ruthenium(II) complexes

  摘要：

  Two ruthenium(II) mixed ligand complexes [Ru(bpy)(2)(imiphen)](PF6)(2), 1 and [Ru(bpy)(2)(phimiphen)](PF6)(2), 2, where imiphen = 2-(1H-imidazol-2yl)-1H-imidazo[4,5-F][1,10]phenanthroline and phimiphen = 2-(1H-benzimidazol-2yl)-1H-imidazo[4,5-F][1,10]phenanthroline have been synthesized and characterized using various spectroscopic techniques like ESI mass, electronic spectroscopy and fluorescence spectroscopy. Both these complexes exhibit unusual fluorescence spectra. Complexes 1 and 2 show emission maxima at 620 and 617 nm when excited at their MLCT band at 450 nm. The emission intensity has been found to depend on the nature of the solvent. Emission intensity of the aqueous solution of complexes 1 and 2 has been found to be 75-143% greater than the emission intensity of acetonitrile solution of these two complexes. This increase in the emission intensity in aqueous solution is accompanied by an increase in the lifetime of the excited state of the complex in aqueous solution. Emission intensity increase observed for these complexes is due to the involvement of the H2O molecule in the hydrogen bonding with imidazole N-H of the ligand, making the ligand rigid. On the other hand, in acetonitrile medium because of lack of hydrogen bonding, the imidazole ring can have free rotation. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.03.026
• 作为产物：
  描述：

  苯并咪唑-2-甲醛 、 1,10-邻二氮杂菲-5,6-二酮 在 乙酸铵 、 L-脯氨酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 2-(1H-benzimidazol-2yl)-1H-imidazo[4,5-F][1,10]phenanthroline
  参考文献：
  名称：

  Unusual solvent dependent emission property of two new ruthenium(II) complexes

  摘要：

  Two ruthenium(II) mixed ligand complexes [Ru(bpy)(2)(imiphen)](PF6)(2), 1 and [Ru(bpy)(2)(phimiphen)](PF6)(2), 2, where imiphen = 2-(1H-imidazol-2yl)-1H-imidazo[4,5-F][1,10]phenanthroline and phimiphen = 2-(1H-benzimidazol-2yl)-1H-imidazo[4,5-F][1,10]phenanthroline have been synthesized and characterized using various spectroscopic techniques like ESI mass, electronic spectroscopy and fluorescence spectroscopy. Both these complexes exhibit unusual fluorescence spectra. Complexes 1 and 2 show emission maxima at 620 and 617 nm when excited at their MLCT band at 450 nm. The emission intensity has been found to depend on the nature of the solvent. Emission intensity of the aqueous solution of complexes 1 and 2 has been found to be 75-143% greater than the emission intensity of acetonitrile solution of these two complexes. This increase in the emission intensity in aqueous solution is accompanied by an increase in the lifetime of the excited state of the complex in aqueous solution. Emission intensity increase observed for these complexes is due to the involvement of the H2O molecule in the hydrogen bonding with imidazole N-H of the ligand, making the ligand rigid. On the other hand, in acetonitrile medium because of lack of hydrogen bonding, the imidazole ring can have free rotation. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.03.026

文献信息

• Inhibition of Aβ peptide aggregation by ruthenium(II) polypyridyl complexes through copper chelation
  作者：Yan-Bo Peng、Can Tao、Cai-Ping Tan、Ping Zhao

  DOI：10.1016/j.jinorgbio.2021.111591

  日期：2021.11

  is known as a complex multifactorial syndrome and both metal chelators and amyloid β peptide (Aβ) inhibitors show promise against AD. Herein, four small hybrid compounds have been designed and synthesized utilizing 8-hydroxyquinoline, pyridine or imidazole as chelators and benzimidazole as the recognition moiety for AD treatment. These conjugates can capture Cu2+ from Aβ and become dimers upon Cu2+ coordination

  阿尔茨海默病 (AD) 被称为复杂的多因素综合征，金属螯合剂和淀粉样蛋白 β 肽 (Aβ) 抑制剂均显示出对抗 AD 的前景。在此，利用 8-羟基喹啉、吡啶或咪唑作为螯合剂，苯并咪唑作为 AD 治疗的识别部分，设计和合成了四种小型杂化化合物。这些共轭物可以从 Aβ捕获 Cu 2+并在 Cu 2+配位时变成二聚体，并且对 Cu 2+都显示出高效率消除和 Aβ 组装抑制。此外，这些设计的复合物可以抑制Aβ诱导的活性氧（ROS）的产生，保护线粒体免受损伤，提高神经元细胞的存活率。我们的工作提供了一种结合疏水相互作用和金属离子螯合来设计淀粉样蛋白抑制剂的新策略。