2-(4-fluorophenyl)-1-p-tolyl-1H-imidazo[4,5-f][1,10]phenanthroline | 1415929-66-6

• 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: 2-(4-fluorophenyl)-1-p-tolyl-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-(4-Fluorophenyl)-3-(4-methylphenyl)imidazo[4,5-f][1,10]phenanthroline；2-(4-fluorophenyl)-3-(4-methylphenyl)imidazo[4,5-f][1,10]phenanthroline
• CAS: 1415929-66-6
• 化学式: C₂₆H₁₇FN₄
• 分子量: 404.446
• InChiKey: VSYBETUJAVXIHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dichloro(tetramethylcyclopentadienylbenzene)iridium(III)dimer 、 2-(4-fluorophenyl)-1-p-tolyl-1H-imidazo[4,5-f][1,10]phenanthroline 、 ammonium hexafluorophosphate 以 甲醇 为溶剂， 以54.3 %的产率得到
  参考文献：
  名称：

  阳离子/中性半夹心铱(III)咪唑-菲咯啉/菲配合物的设计及其抗癌行为

  摘要：

  有机金属铱（III）（Ir）配合物作为金属抗癌药物的潜力受到了相当多的关注。在本研究中，制备并表征了 12 个半夹心 Ir 咪唑-菲咯啉/菲配合物。复合物表现出良好的抗增殖活性，其中一些复合物对A549细胞的抑制作用明显优于顺铂。这些复合物具有合适的荧光，并且确定了非能量依赖性摄取途径，随后导致它们在溶酶体中积累并造成溶酶体损伤。此外，复合物可以抑制细胞周期（G1期）并催化细胞内NADH氧化，从而证实细胞内活性氧（ROS）水平升高，从而证实了氧化机制。 Western blotting进一步证实复合物可以通过溶酶体-线粒体抗癌途径诱导A549细胞凋亡，这与顺铂不一致。总之，这些配合物为有机金属非铂抗癌药物的开发提供了新的概念。

  DOI：

  10.1016/j.jinorgbio.2024.112612
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 、 对氟苯甲醛 、 乙烷,三氯氟- 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 以50%的产率得到2-(4-fluorophenyl)-1-p-tolyl-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  Physico-chemical studies of fused phenanthrimidazole derivative as sensitive NLO material

  摘要：

  Heterocyclic phenanthrimidazole derivative, 2-(4-fluorophenyl)-1-p-tolyl-1H-imidazo[4,5-f] [1,10] phenanthroline (FPTIP) has been synthesized and characterised by NMR, mass and CHN analysis. The FFTIP was evaluated concerning their solvatochromic properties and molecular optical nonlinearities. Their electric dipole moment (mu), polarizability (alpha) and hyperpolarizability (beta) have been calculated theoretically and the results indicate that the extension of the pi-framework of the ligands has an effect on the NLO properties. The energies of the HOMO and LUMO levels and the molecular electrostatic potential (MEP) energy surface studies have exploited the existence of intramolecular charge transfer (ICT) within the molecule. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.09.089

文献信息

• Physico-chemical studies of fused phenanthrimidazole derivative as sensitive NLO material
  作者：Jayaraman Jayabharathi、Venugopal Thanikachalam、Ramalingam Sathishkumar、Karunamoorthy Jayamoorthy

  DOI：10.1016/j.saa.2012.09.089

  日期：2013.1

  Heterocyclic phenanthrimidazole derivative, 2-(4-fluorophenyl)-1-p-tolyl-1H-imidazo[4,5-f] [1,10] phenanthroline (FPTIP) has been synthesized and characterised by NMR, mass and CHN analysis. The FFTIP was evaluated concerning their solvatochromic properties and molecular optical nonlinearities. Their electric dipole moment (mu), polarizability (alpha) and hyperpolarizability (beta) have been calculated theoretically and the results indicate that the extension of the pi-framework of the ligands has an effect on the NLO properties. The energies of the HOMO and LUMO levels and the molecular electrostatic potential (MEP) energy surface studies have exploited the existence of intramolecular charge transfer (ICT) within the molecule. (C) 2012 Elsevier B.V. All rights reserved.
• 10.1016/j.jinorgbio.2024.112612
  作者：Lv, Ao、Li, Guangxiao、Zhang, Pei、Tao, Rui、Li, Xiaoshuang、Ren, Xueyan、Li, Peixuan、Liu, Xicheng、Yuan, Xiang-Ai、Liu, Zhe

  DOI：10.1016/j.jinorgbio.2024.112612

  日期：——

  the exploration of organometallic iridium(III) (Ir) complexes for their potential as metallic anticancer drugs. In this study, twelve half-sandwich Ir imidazole-phenanthroline/phenanthrene complexes were prepared and characterized. Complexes exhibited promising anti-proliferative activity, and some are obviously superior to cisplatin towards A549 cells. These complexes possessed suitable fluorescence

  有机金属铱（III）（Ir）配合物作为金属抗癌药物的潜力受到了相当多的关注。在本研究中，制备并表征了 12 个半夹心 Ir 咪唑-菲咯啉/菲配合物。复合物表现出良好的抗增殖活性，其中一些复合物对A549细胞的抑制作用明显优于顺铂。这些复合物具有合适的荧光，并且确定了非能量依赖性摄取途径，随后导致它们在溶酶体中积累并造成溶酶体损伤。此外，复合物可以抑制细胞周期（G1期）并催化细胞内NADH氧化，从而证实细胞内活性氧（ROS）水平升高，从而证实了氧化机制。 Western blotting进一步证实复合物可以通过溶酶体-线粒体抗癌途径诱导A549细胞凋亡，这与顺铂不一致。总之，这些配合物为有机金属非铂抗癌药物的开发提供了新的概念。