2-(4-fluorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline | 1233850-93-5

• 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: 2-(4-fluorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-(4-Fluoro-phenyl)-1h-imidazo[4,5-f][1,10]phenanthroline
• CAS: 1233850-93-5
• 化学式: C₁₉H₁₁FN₄
• 分子量: 314.322
• InChiKey: FTSCIJYRLIDZLF-UHFFFAOYSA-N

物化性质

• 沸点：
  596.4±60.0 °C(Predicted)
• 密度：
  1.433±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 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：
  54.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [RuCl2(benzene)]2 、 2-(4-fluorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline 以 二氯甲烷 为溶剂， 反应 0.5h， 以90.8%的产率得到[(η⁶-C₆H₆)ruthenium(II)(p-2-(4-fluorophenyl)imidazole[4,5-f ][1,10]-phenanthroline)Cl]Cl
  参考文献：
  名称：

  Arene Ruthenium(II) Complexes as Low-Toxicity Inhibitor against the Proliferation, Migration, and Invasion of MDA-MB-231 Cells through Binding and Stabilizing c-myc G-Quadruplex DNA

  摘要：

  Arene Ru(II) complexes have long been extensively studied as potential inhibitors against the proliferation of tumor cells, but their behavior against the migration and invasion of tumor cells needs further research. In this work, a series of arene Ru(II) complexes, (n(6-)C(6)H(6))Ru(p-XPIP)Cl]Cl (X = H, 1; F, 2; Cl, 3; Br, 4; and I, 5), have been synthesized, and their inhibitory activity against the migration and invasion of MDA-MB-231 breast cancer cells have been investigated. It is found that all of these complexes exhibit excellent inhibitory activity (IC50) against the growth of MDA-MB-231 breast cancer cells, and the value of IC50 for 1, 2, 3, 4, and 5 is about >300, 52.6, 11.4, 45.5, and 59.1 mu M, respectively. Further studies by wound-healing assay, FITC-geltain assay, and flow cytometry assay showed that 3 can apparently suppress the migration and invasion of MDA-MB-231 cells via the joint action of S-phase arrest and apoptosis. Moreover, the binding behavior of these arene Ru(II) complexes with c-myc G-quadruplex DNA has also been studied, and the results showed that these complexes can bind and stabilize c-myc Gquadruplex DNA in groove binding mode. Also, the low toxicity of 3 was confirmed by its low inhibitory activity against the growth of normal MCF-10A breast cells in vitro and the development of zebrafish embryos in vivo. In other words, these results indicated that synthetic arene Ru(II) complexes can be developed as low-toxicity agents against the proliferation, migration, and invasion of breast cancer cells.

  DOI：

  10.1021/acs.organomet.5b00820
• 作为产物：
  描述：

  1,10-菲罗啉 在 硫酸 、 ammonium acetate 、 硝酸 、 溶剂黄146 、 potassium bromide 作用下， 反应 0.33h， 生成 2-(4-fluorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  菲并咪唑衍生物通过激活DNA损伤途径作为自噬的潜在诱导剂。

  摘要：

  本研究合成了一系列咪唑并[4,5f] [1,10]菲咯啉衍生物（1-6），并通过MTT法对其抑菌活性进行了评价。结果表明，所有这些化合物均显示出对一组人类癌细胞系的有希望的抑制活性。该化合物6是最有效的化合物，IC50约为2.3±0.1 µM，对生长不利，可诱导HepG2细胞自噬。通过在细胞中出现大量自噬空泡以及在透射电子显微镜下观察到的明显的超微结构变化，证实了这种情况。通过上调LC3-II和Beclin1也证明了6诱导的自噬。在对HepG2细胞进行6次处理后，还证实了通过DSB损伤引起的凋亡和G2 / M期细胞周期停滞。这些多重效应，

  DOI：

  10.1016/j.bioorg.2019.102940

文献信息

• Luminescent ruthenium(II)-para-cymene complexes of aryl substituted imidazo-1,10-phenanthroline as anticancer agents and the effect of remote substituents on cytotoxic activities
  作者：Sourav De、R. Selva Kumar、Ashna Gauthaman、S.K. Ashok Kumar、Priyankar Paira、Anbalagan Moorthy、Subhasis Banerjee

  DOI：10.1016/j.ica.2020.120066

  日期：2021.1

  Abstract Ruthenium complexes are currently significant attention in medicinal chemistry as they offer various properties which make them an appropriate choice for drug development. Herein, a series of ruthenium(II)-p-cymene-2-aryl-imidazo-1,10-phenanthroline derivatives have been prepared and characterised by elemental analysis, infrared, LC-mass and NMR techniques. The structural and chemical properties

  摘要钌配合物目前在药物化学中备受关注，因为它们具有多种特性，使其成为药物开发的合适选择。本文中，已经制备了一系列钌（II）-对-异丙基-2-芳基-咪唑基-1,10-菲咯啉衍生物，并通过元素分析，红外，LC-质谱和NMR技术对其进行了表征。结构和化学性质表明，Ru（II）配合物具有刚性，平面性，芳香性，给氢和接受氢的能力，有助于溶解性和与生物分子的相互作用。这些复合物与DNA和BSA的结合强度为104–106 M-1。在络合物存在下，溴化乙锭（EtBr）从DNA的竞争性置换揭示出插层或凹槽结合，这进一步受到粘度和计算机模拟研究的支持。这些Ru（II）复合物的细胞毒性研究是用两种癌细胞系（MDA-MB-231和HeLa）和一种人类胚胎肾细胞（HEK-293）进行的。研究表明，[（η6-p-cymene）RuCl（κ2-N，N-2-（4-氟苯基）-1H-咪唑并[4,5-f] [1,10]菲咯啉]
• 一种芳烃钌配合物及其制备方法与应用
  申请人：广东药科大学

  公开号：CN107793454B

  公开（公告）日：2020-05-05

  本发明公开了一种芳烃钌配合物，采用R1R2R3PIP为主配体，所述R1、R2、R3独立地选自‑Cl,‑F,‑Br,‑I,‑CF3,‑NO2,‑OCH3,‑OH,‑COOH,‑CH3,‑N(CH3)2,‑C2H2,‑SO2CH3、碳原子数为1～6的烷基或碳原子为1～6的取代烷基、吡啶基或取代吡啶基、呋喃基或取代呋喃基、吡咯基或取代吡咯基、噻唑或取代噻唑基；其中，所述苯基、吡啶基、呋喃基、噻唑的取代基均独立的选自羟基、硝基、卤素、氨基、羧基、氰基、巯基、碳原子数为3～8的环烷基、SO3H、碳原子数为1～6的烷基、碳原子数为2～6的链烯基、碳原子为2～6的链炔基、羟基(C1‑C6)烷基、氨基(C1‑C6)烷基、CO2R’、CONR’R’、COR’、SO2R’R’、(C1‑C6)烷氧基、(C1‑C6)烷硫基、‑N＝NR’、NR’R’或三氟(C1‑C6)烷基中的任一种。
• Imidazo [4,5f][1,10] phenanthroline derivatives as inhibitor of c-myc gene expression in A549 cells via NF-κB pathway
  作者：Dong-dong Sun、Wei-zhang Wang、Jian-wen Mao、Wen-jie Mei、Jie Liu

  DOI：10.1016/j.bmcl.2011.11.063

  日期：2012.1

  1,10-Phenanthroline has been shown to exhibit anticancer activity. Here, a series of imidazo [4,5f][1,10] phenanthroline derivatives 1−10 were synthesized and their biological activities were further elucidated. We found that 2-(4-Brominephenyl)-imidazo [4,5f][1,10] phenanthroline (compound 3) possessed potent antiproliferation activities again a variety of tumor cell lines using 3-(4,5-dimethyl-2-thiazolyl)-2

  1,10-菲咯啉已显示出抗癌活性。在这里，合成了一系列咪唑并[4,5 f ] [1,10]菲咯啉衍生物1-10，并进一步阐明了它们的生物学活性。我们发现2-（4-溴苯基）-咪唑并[4,5 f ] [1,10]菲咯啉（化合物3）在使用3-（4,5-二甲基-2 -噻唑基）-2,5-二苯基溴化四氮唑（MTT）分析。流式细胞仪分析显示，化合物3通过人肺腺癌细胞系A549的凋亡和坏死诱导。此外，化合物3这种治疗导致A549细胞中IκBα的上调以及p65和c-myc的下调。综上所述，这些结果表明化合物3通过抑制NF-κB活性和下调c-myc基因表达来抑制细胞增殖，并且可能作为人癌症，尤其是肺癌的化学预防和化学治疗剂而进一步评估的候选者。癌症。
• Synthesis of Fluorinated Imidazole[4,5 <i>f</i> ][1,10]phenanthroline Derivatives as Potential Inhibitors of Liver Cancer Cell Proliferation by Inducing Apoptosis via DNA Damage
  作者：Ming‐Jun Bai、Ning‐Zhi Liu、Yu‐Ling Zhou、Jie Liu、Jun Zou、Wei‐Jun Tan、Xiao‐Ting Huang、Wen‐Jie Mei

  DOI：10.1002/cmdc.202100537

  日期：2022.2.16

  Blocking cancer cell growth: Fluorinated imidazole[4,5f][1,10]phenanthroline derivative 4 (shown) can effectively inhibit the growth of HepG2 cells by inducing apoptosis via DNA damage. Our findings provideguidance for further optimization of imidazole phenanthroline derivatives and the development of potential anticancer agents.

  阻断癌细胞生长：氟化咪唑[4,5f][1,10]菲咯啉衍生物4（如图所示）可通过DNA损伤诱导细胞凋亡，从而有效抑制HepG2细胞的生长。我们的研究结果为进一步优化咪唑菲咯啉衍生物和开发潜在的抗癌药物提供了指导。
• Synthesis, docking studies and antitumor activity of phenanthroimidazole derivatives as promising c-myc G-quadruplex DNA stabilizers
  作者：Qiong Wu、Yue Song、Ruotong Liu、Rui Wang、Wenjie Mei、Weiming Chen、Huanglan Yang、Xicheng Wang

  DOI：10.1016/j.bioorg.2020.104074

  日期：2020.9

  Phenanthroimidazole derivatives containing phenanthroline and imidazole heterocyclic aromatic rings are effective agents to inhibit tumor cell growth. Herein, halogen element-modified imidazo[4,5f][1,10]phenanthroline derivatives 1–6 (1, 4-fluorophenyl; 2, 4-chlorophenyl; 3, 4-bromobenyl; 4, 2,3-dichlorophenyl; 5, 3,4-dichlorophenyl; and 6, 2,4-dichlorophenyl) were synthesized, and their antitumor activities were

  含有菲咯啉和咪唑杂环芳环的菲并咪唑衍生物是抑制肿瘤细胞生长的有效药物。在本文中，卤族元素改性的咪唑并[4,5 ˚F ] [1,10]菲咯啉衍生物1-6（1，4-氟苯基; 2，4-氯苯基; 3，4- bromobenyl; 4，2,3-二氯苯基; 5，3,4-二氯苯基;和6，2,4-二氯苯基）的合成，和它们的抗肿瘤活性进行了研究。所有化合物，特别是4种化合物，对鼻咽癌CNE-1细胞均表现出优异的抑制作用。该作用优于阿霉素。复合图4还显着阻断了斑马鱼异种移植模型中CNE-1细胞的增殖。该抗肿瘤机制可能归因于细胞凋亡的诱导，其通过稳定c-myc G-四链体DNA结构引发ROS介导的DNA损伤并产生线粒体功能障碍。结果表明菲并咪唑衍生物可以作为有希望的抗癌药。