(E)-2-styryl-1H-imidazo[4,5-f][1,10]phenanthroline

• 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: (E)-2-styryl-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-[(E)-2-phenylethenyl]-1H-imidazo[4,5-f][1,10]phenanthroline
• 化学式: C₂₁H₁₄N₄
• 分子量: 322.369
• InChiKey: FCUMYTXQSREJBM-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  copper(II) nitrate trihydrate 、 (E)-2-styryl-1H-imidazo[4,5-f][1,10]phenanthroline 以 乙醇 为溶剂， 反应 0.5h， 生成 [Cu((E)-2-styryl-1H-imidazo[4,5-f][1,10]phenanthroline)₂](NO₃)₂
  参考文献：
  名称：

  Spectroscopic analysis, DNA binding and antimicrobial activities of metal complexes with phendione and its derivative

  摘要：

  A novel ligand (E)-2-styryl-1H-imidazo [4, 5-f] [1, 10] phenanthroline(L) has been synthesized from 1,10-phenanthroline-5,6-dione. Its transition metal complexes, [FeLCl4][L-H] and [CuL2](NO3)(2) have also been synthesized. Besides, three mixed ligand lanthanide metal complexes of Phendione and beta-diketones have been synthesized, namely [Eu(TFN)(3)(Phendione)] (TFN = 4,4,4-trifluoro-1(2-napthyl)-1,3-butanedione), Eu(HFT)(3)(Phendione)] (HFT = 4,4,5,5,6,6,6-heptafluoro-1-(2-thienyl)-1,3-hexanedione), [Yb(HFA)(3)(Phendione)] (hfa = hexafluoroacetylacetonate). The synthesized ligands and metal complexes have been characterized by FTIR, UV-Visible spectroscopy and PL spectra. DNA binding activities of the complexes and the ligands have been studied by DNA gel electrophoresis. DNA binding studies showed that Fe complex of the synthesized ligand is more potent DNA binding and damaging agent compare to others under study. The synthesized compounds were also screened for their antimicrobial activities by disc diffusion method against three microbes, namely Escherichia coli, Staphylococcus aureus, Proteus penneri. The lanthanide complexes of phendione showed great antibacterial activities. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2013.09.110
• 作为产物：
  描述：

  反式肉桂醛 、 1,10-邻二氮杂菲-5,6-二酮 在 ammonium acetate 、 溶剂黄146 作用下， 反应 2.0h， 以65%的产率得到(E)-2-styryl-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  新型聚吡啶钌复合物，可作为高亲和力DNA嵌入剂，有效的转录抑制剂和抗肿瘤试剂。

  摘要：

  设计了六种新颖的具有（E）-2-styryl-1H-咪唑并[4,5-f] [1,10]菲咯啉配体及其类似物的聚吡啶钌配合物，以增强其模型化合物[Ru（ bpy）2（pip）] 2+（bpy = 2,2'-联吡啶，pip = 2-苯基-1H-咪唑并[4,5-f] [1,10]菲咯啉）。如配合物的最佳几何形状所示，苯乙烯基的引入不仅扩展了插入配体的共轭面积，而且保留了优异的平面度。这两个优点已被证明对它们的DNA插入有益，因此大大提高了它们对RNA聚合酶和DNA拓扑异构酶对DNA转录的抑制活性，这两种酶与DNA和肿瘤细胞的生长密切相关。还通过量子化学计算从能量和电子方面研究了取代基基团结构与生物活性之间的关系。细胞细胞毒性和凋亡测定的结果证明，苯乙烯基取代的钌配合物具有比[Ru（bpy）2（pip）] 2+更高的抗肿瘤活性。如MTT（3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑鎓溴化

  DOI：

  10.1016/j.jinorgbio.2018.04.019

文献信息

• Induction of apoptosis in SGC-7901 cells by iridium(III) complexes via endoplasmic reticulum stress-mitochondrial dysfunction pathway
  作者：Jiawen Wang、Haimei Liu、Xiaoyun Wu、Chuanling Shi、Wenlong Li、Yuhan Yuan、Yunjun Liu、Degang Xing

  DOI：10.1007/s00775-022-01943-6

  日期：——

  method. We found that the complexes 1, 2 and 3 significantly inhibited cell proliferation, in particular, complexes 2 and 3 show high cytotoxic effect on SGC-7901 cells with an IC50 value of 5.8 ± 0.7 and 4.4 ± 0.1 μM. Moreover, cell cycle assay revealed that the complexes could block G2/M phase of the cell cycle. Apoptotic evaluation by Annexin V/PI staining indicated that complexes 1–3 can induce apoptosis

  本研究旨在评估三种新合成的铱 (III) 配合物 [Ir(ppy) 2 (PEIP)](PF 6 ) ( 1 ) (ppy = 2-phenylpyridine, PEIP = 2-phenethyl-1 H ) 的抗癌活性-咪唑[4,5-f][1,10]菲咯啉), [Ir(ppy) 2 (SIP)](PF 6 ) ( 2 ) (SIP = (E)-2-styryl-1 H -咪唑[ 4,5-f][1,10]菲咯啉）和[Ir(ppy) 2 (PEYIP)](PF 6 ) ( 3 ) (PEYIP = 2-phenethynyl-1 H-咪唑[4,5-f][1,10]菲咯啉）。采用 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) 方法研究了对 A549、SGC-7901、HepG2、HeLa 和正常 NIH3T3
• 一种肉桂醛衍生物及其制备方法和应用
  申请人：广州鲁比生物科技有限公司

  公开号：CN114671870A

  公开（公告）日：2022-06-28

  本发明涉及抗肿瘤药物技术领域，提供了一种肉桂醛衍生物及其制备方法和应用。本发明提供的肉桂醛衍生物是一种肉桂醛修饰的菲并咪唑衍生物，结构新颖，对肿瘤细胞的生长具有抑制效果，且对正常细胞的毒性较低，为制备选择性抑制肿瘤细胞、对正常细胞毒性较低的肉桂醛衍生物类药物打下坚实的基础，具有潜在的产业化开发价值，对抗癌药物的研究具有重大意义。本发明提供的制备方法所用原料安全，所需设备简单，操作简单易行，纯化方法简单，产率较高，容易进行工业化生产。
• Spectroscopic analysis, DNA binding and antimicrobial activities of metal complexes with phendione and its derivative
  作者：Md Abdus Subhan、Md. Saifur Rahman、Khyrul Alam、Md. Mahmud Hasan

  DOI：10.1016/j.saa.2013.09.110

  日期：2014.1

  A novel ligand (E)-2-styryl-1H-imidazo [4, 5-f] [1, 10] phenanthroline(L) has been synthesized from 1,10-phenanthroline-5,6-dione. Its transition metal complexes, [FeLCl4][L-H] and [CuL2](NO3)(2) have also been synthesized. Besides, three mixed ligand lanthanide metal complexes of Phendione and beta-diketones have been synthesized, namely [Eu(TFN)(3)(Phendione)] (TFN = 4,4,4-trifluoro-1(2-napthyl)-1,3-butanedione), Eu(HFT)(3)(Phendione)] (HFT = 4,4,5,5,6,6,6-heptafluoro-1-(2-thienyl)-1,3-hexanedione), [Yb(HFA)(3)(Phendione)] (hfa = hexafluoroacetylacetonate). The synthesized ligands and metal complexes have been characterized by FTIR, UV-Visible spectroscopy and PL spectra. DNA binding activities of the complexes and the ligands have been studied by DNA gel electrophoresis. DNA binding studies showed that Fe complex of the synthesized ligand is more potent DNA binding and damaging agent compare to others under study. The synthesized compounds were also screened for their antimicrobial activities by disc diffusion method against three microbes, namely Escherichia coli, Staphylococcus aureus, Proteus penneri. The lanthanide complexes of phendione showed great antibacterial activities. (C) 2013 Elsevier B.V. All rights reserved.
• Novel polypyridyl ruthenium complexes acting as high affinity DNA intercalators, potent transcription inhibitors and antitumor reagents
  作者：Guo-Lan Ma、Xu-Dan Bi、Feng Gao、Zheng Feng、Dong-Chun Zhao、Feng-Jie Lin、Ru Yan、Dandan Liu、Peng Liu、Jingbo Chen、Hongbin Zhang

  DOI：10.1016/j.jinorgbio.2018.04.019

  日期：2018.8

  enzymes closely related to both DNA and tumor cell growth. The relationships between the substituent group structures and the biological activities have also been investigated from energetic and electronic aspects by quantum chemistry calculations. Results from cell cytotoxicity and apoptosis assay testified that the styryl substituted ruthenium complexes possessed higher antitumor activity than [Ru(bpy)2(pip)]2+

  设计了六种新颖的具有（E）-2-styryl-1H-咪唑并[4,5-f] [1,10]菲咯啉配体及其类似物的聚吡啶钌配合物，以增强其模型化合物[Ru（ bpy）2（pip）] 2+（bpy = 2,2'-联吡啶，pip = 2-苯基-1H-咪唑并[4,5-f] [1,10]菲咯啉）。如配合物的最佳几何形状所示，苯乙烯基的引入不仅扩展了插入配体的共轭面积，而且保留了优异的平面度。这两个优点已被证明对它们的DNA插入有益，因此大大提高了它们对RNA聚合酶和DNA拓扑异构酶对DNA转录的抑制活性，这两种酶与DNA和肿瘤细胞的生长密切相关。还通过量子化学计算从能量和电子方面研究了取代基基团结构与生物活性之间的关系。细胞细胞毒性和凋亡测定的结果证明，苯乙烯基取代的钌配合物具有比[Ru（bpy）2（pip）] 2+更高的抗肿瘤活性。如MTT（3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑鎓溴化