2-(4-chlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline | 185129-90-2

• 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-chlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-(4-chlorophenyl)imidazo[4,5-f][1,10]phenanthroline；cpip；2-(4'-Chloro-phenyl) imidazo[4,5-f][1,10]phenanthroline
• CAS: 185129-90-2
• 化学式: C₁₉H₁₁ClN₄
• 分子量: 330.776
• InChiKey: AVYYURWQBJQNLD-UHFFFAOYSA-N

物化性质

• 熔点：
  307-308 °C
• 沸点：
  619.9±65.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：
  3

反应信息

• 作为反应物：
  描述：

  [RuCl2(benzene)]2 、 2-(4-chlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline 以 二氯甲烷 为溶剂， 反应 0.5h， 以90.4%的产率得到[(η⁶-C₆H₆)ruthenium(II)(p-2-(4-chlorophenyl)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：

  4-氯苯乙烯 在 叔丁基过氧化氢 、 C₃₀H₂₉ClN₄ORu⁽²⁺⁾*2F₆P^(1-) 、 ammonium acetate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 2-(4-chlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  远程基于“咪唑”的钌（II）对伞花烃预催化剂，可选择性氧化裂解CC多个键

  摘要：

  远端'咪唑'与预催化剂[（对-cymene）Ru II（L）Y] +（L = 2-（4-取代-苯基）-1H-咪唑[4,5-f] [探索了1,10]菲咯啉（Y =氯化物/溶剂）用于CC多键缩醛/醛的选择性氧化裂解。发现预催化剂中存在“咪唑”可用于活化氧化剂和从预催化剂中释放对苯甲基异丙基苯，反过来，如果没有“咪唑”部分，则这是无效的。从光谱，动力学和其他一些受控实验中评估了预催化剂的机理。对苯甲基苯甲酸酯的损失是反应的关键步骤，在溶剂化的预催化剂中发现更快，[[p- cymene）Ru II（L）（MeOH）] ++，因此比[[ p- cymene）Ru II（L）Cl] +效果高3-4倍。

  DOI：

  10.1002/cctc.201900242

文献信息

• A Remote ‘Imidazole’‐Based Ruthenium(II) Para‐Cymene Pre‐catalyst for the Selective Oxidation Reaction of Alkyl Arenes and Alcohols
  作者：Manali Dutta、Kusum K. Bania、Sanjay Pratihar

  DOI：10.1002/asia.201901760

  日期：2020.3.16

  the 'imidazole' moiety. The mechanistic features of C-1 promoted oxidation of alkyl arenes were also assessed from spectroscopic, kinetic, and few control experiments. The substrate scope for C-1 promoted oxidation reaction was assessed based on the selective oxidation of 27-different alkyl arenes/heteroarenes and 25 different alcohols to their corresponding aldehydes/ketones in moderate to good yields

  本文中，我们公开了使用基于远程'咪唑'的预催化剂[（对-异丙基）RuII（L）Cl] + C-1，其中L = 2-（4-取代-苯基）-1H-咪唑[4， 5-f] [1,10]菲咯啉），用于在叔丁基氢过氧化物（TBHP）存在下将各种烷基芳烃/杂芳烃和醇选择性氧化为相应的醛或酮。配合物中存在的远端“咪唑”部分通过从C-1释放对伞花酸促进氧化剂的活化和活性物质的后续生成，而没有“咪唑”部分则反过来效果较差。还通过光谱，动力学和少量对照实验评估了C-1促进烷基芳烃氧化的机理。
• Oxovanadium phenanthroimidazole derivatives: synthesis, DNA binding and antitumor activities
  作者：Yin-Liang Bai、Ya-Wu Zhang、Ji-Yuan Xiao、Hai-Wei Guo、Xiang-Wen Liao、Wen-Jie Li、You-Cheng Zhang

  DOI：10.1007/s11243-018-0205-9

  日期：2018.3

  HPIP = 2-(4-hydroxylphenyl)-imidazo[4,5-f] 1,10-phenanthroline), have been synthesized and characterized. Their DNA binding and antitumor activities were determined by biochemical methods. All four oxovanadium complexes can bind with CT-DNA by an intercalation model and can also cleave supercoiled plasmid DNA in the presence of H2O2. The antitumor properties and mechanism of the complexes have been analyzed by

  四种不对称氧钒菲咪唑配合物，[VO(hntdtsc)(NPIP)] (1), [VO(hntdtsc)(CPIP)] (2), [VO(hntdtsc)(MEPIP)] (3) 和 [VO(hntdtsc) (HPIP)] (4) (hntdtsc = 2-羟基-1-萘甲醛缩氨基硫脲，NPIP = 2-(4-硝基苯基)-咪唑并[4,5-f]1,10-菲咯啉，CPIP = 2-(4-氯苯基)-咪唑并[4,5-f]1,10-菲咯啉), MEPIP = 2-(4-甲基苯基)-咪唑并[4,5-f]1,10-菲咯啉), HPIP = 2-(4-羟基苯基)-咪唑并[4,5-f] 1,10-菲咯啉)，已被合成和表征。它们的 DNA 结合和抗肿瘤活性是通过生化方法测定的。所有四种氧钒复合物都可以通过嵌入模型与 CT-DNA 结合，并且还可以在 H2O2 存在下切割超螺旋质粒 DNA。通过MTT法、细胞周期
• Towards the Development of Photo‐Reactive Ruthenium(II) Complexes Targeting Telomeric G‐Quadruplex DNA
  作者：Justin Weynand、Aurélie Diman、Michaël Abraham、Lionel Marcélis、Hélène Jamet、Anabelle Decottignies、Jérôme Dejeu、Eric Defrancq、Benjamin Elias

  DOI：10.1002/chem.201804771

  日期：2018.12.20

  characterization of new ruthenium(II) complexes aimed at targeting G‐quadruplex DNA is reported. Importantly, these complexes are based on oxidizing 1,4,5,8‐tetraazaphenanthrene (TAP) ancillary ligands known to favour photo‐induced electron transfer (PET) with DNA. The photochemistry of complexes 1–4 has been studied by classical methods, which revealed two of them to be capable of photo‐abstracting an electron

  报道了针对G-四链体DNA的新钌（II）配合物的设计和表征。重要的是，这些络合物是基于氧化1,4,5,8-四氮杂菲（TAP）辅助配体而形成的，这些配体有利于DNA的光诱导电子转移（PET）。复合物的光化学1 - 4已通过经典方法进行了研究，发现其中两种方法能够从鸟嘌呤中吸收电子。从通过发光，圆二色性，生物层干涉和表面等离振子共振实验研究与DNA的相互作用中，我们证明了这些复合物对端粒G-四链体DNA的选择性高于双链体DNA。已对这些复合物进行了初步的生物学研究：其中两个显示出对端粒酶阴性的U2OS骨肉瘤细胞具有显着的光细胞毒性，而在相同光药物浓度下，在黑暗中观察到极低的死亡率。
• Cyclometalated Iridium(III) Imidazole Phenanthroline Complexes as Luminescent and Electrochemiluminescent G-Quadruplex DNA Binders
  作者：Katherine J. Castor、Kimberly L. Metera、Ushula M. Tefashe、Christopher J. Serpell、Janine Mauzeroll、Hanadi F. Sleiman

  DOI：10.1021/acs.inorgchem.5b00921

  日期：2015.7.20

  Six cyclometalated iridium(III) phenanthroimidazole complexes with different modifications to the imidazole phenanthroline ligand exhibit enhanced luminescence when bound to guanine (G-) quadruplex DNA sequences. The complexes bind with low micromolar affinity to human telomeric and c-myc sequences in a 1:1 complex:quadruplex stoichiometry. Due to the luminescence enhancement upon binding to G-quadruplex

  当与鸟嘌呤（G-）四重体DNA序列结合时，对咪唑菲咯啉配体具有不同修饰的六个环金属化铱（III）菲并咪唑配合物显示出增强的发光。配合物以低的微摩尔亲和力与人端粒和c-myc序列以1：1配合物：四链体化学计量比结合。由于与G-四链体DNA结合时的发光增强，因此该复合体可用作选择性四链体指示剂。另外，在特定的G-四链体序列存在下，所有复合物的电化学发光都增加，证明了开发基于ECL的G-四链体测定的潜力。
• 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。