2-(3-aminophenyl)imidazo[4,5-f][1,10]phenanthroline | 1217185-03-9

• 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-(3-aminophenyl)imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 3-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)aniline
• CAS: 1217185-03-9
• 化学式: C₁₉H₁₃N₅
• 分子量: 311.346
• InChiKey: YATAZLJDYJEDJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  80.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氰胺 、 2-(3-aminophenyl)imidazo[4,5-f][1,10]phenanthroline 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 48.5h， 以65.5%的产率得到1-(3-(1H-imidazo[4,5-f] [1,10]phenanthrolin-2-yl)phenyl)guanidine hydrochloride
  参考文献：
  名称：

  Synthesis, characterization and DNA binding studies of two Ru(II) complexes containing guanidinium ligands

  摘要：

  Two new Ru(II) complexes containing guanidinium groups have been synthesized, characterized and analyzed according to their interactions with different G-quadruplexes and duplex DNA. A FRET assay and a competitive FRET assay showed that both complexes promote the formation and stabilization of the human telomeric (h-telo) G-quadruplex and exhibit higher selectivity compared to promoters (such as c-myc, c-kit and bcl2) or duplex DNA. After binding to G-quadruplex, the two complexes have shown different DNA affinity and fluorescence enhancement. CD analyses further indicate that the two complexes display the ability to induce and stabilize the formation of antiparallel G-quadruplex structures in K+, Na+ or ion-free buffers. The binding stoichiometry with h-telo was of the order of three ruthenium complexes per quadruplex. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2016.02.038
• 作为产物：
  描述：

  3-nitrophenyl-1H-imidazo[4,5-f][1,10]phenanthroline 在 palladium on activated charcoal 、 一水合肼 作用下， 生成 2-(3-aminophenyl)imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  钌(II)多吡啶配合物对人胃癌SGC-7901细胞的抗癌活性研究

  摘要：

  摘要 一种新配体 TCPI 及其三个钌 (II) 多吡啶配合物 [Ru(NN)2(TCPI)](PF6)2 (NN = bpy: 2,2'-bipyridine 1; phen: 菲咯啉 2; dmp: 2, 9-二甲基-1,10-菲咯啉3) 被合成并通过元素分析、ESI-MS、1H NMR、IR、吸收和发射光谱表征。通过MTT方法评估配体和复合物对癌细胞SGC-7901、PC-12、HepG-2、SiHa、Eca-109、HeLa和正常细胞LO2的体外细胞毒活性。复合物 3 在复合物中对 SGC-7901 细胞显示出最高的细胞毒活性。有趣的是，复合物对正常细胞 LO2 显示出低或没有细胞毒活性。AO/EB染色法检测SGC-7901细胞凋亡情况。在荧光显微镜和流式细胞术下研究ROS水平和线粒体膜电位的变化。详细研究了细胞侵袭、细胞周期停滞和 Bcl-2 家族蛋白的表达。结果表明，复合物通过

  DOI：

  10.1016/j.inoche.2016.06.020

文献信息

• 一种金属铱(III)配合物及其制备方法和应用
  申请人：广州市第一人民医院（广州消化疾病中心、广州医科大学附属市一人民医院、华南理工大学附属第二医院）

  公开号：CN113512072B

  公开（公告）日：2022-07-01

  本发明公开了一种金属铱(III)配合物及其制备方法和应用，属于医药技术领域。本发明的金属铱(III)配合物包含一价阳离子和一价阴离子。此外，本发明还提出了上述金属铱(III)配合物的制备方法及其在抗肿瘤药物中的应用。本发明的金属铱(III)配合物对肿瘤细胞，特别是B16肿瘤细胞的生长具有很强的抑制作用，其通过调控细胞周期负调控因子P53、P21的表达增加，随后下调Cyclin D1、CDK4和CDK6的表达使得细胞周期转化受阻，细胞增殖被抑制，诱导细胞周期阻滞在G0/G1期，同时其还能诱导B16肿瘤细胞凋亡，有显著的体内抗B16肿瘤细胞活性。
• Synthesis, DNA-binding, photocleavage, cytotoxicity and antioxidant activity of ruthenium (II) polypyridyl complexes
  作者：Yun-Jun Liu、Cheng-Hui Zeng、Hong-Liang Huang、Li-Xin He、Fu-Hai Wu

  DOI：10.1016/j.ejmech.2009.10.043

  日期：2010.2

  Two new ligands maip (1a), paip (1b) with their ruthenium (II) complexes [Ru(bpy)2(maip)](ClO4)2 (2a) and [Ru(bpy)2(paip)](ClO4)2 (2b) have been synthesized and characterized. The results show that complexes 2a and 2b interact with DNA through intercalative mode. The cytotoxicity of these compounds has been evaluated by MTT assay. The experiments on antioxidant activity show that these compounds exhibit

  两个新的配体maip（1a），paip（1b）及其钌（II）络合物[Ru（bpy）2（maip）]（ClO 4）2（2a）和[Ru（bpy）2（paip）]（ClO 4）2（2b）已合成和表征。结果表明，复合物2a和2b通过插入模式与DNA相互作用。这些化合物的细胞毒性已经通过MTT测定法进行了评估。抗氧化剂活性的实验表明，这些化合物对羟基自由基（OH ）表现出良好的抗氧化剂活性。
• Anticancer mechanism studies of iridium(III) complexes inhibiting osteosarcoma HOS cells proliferation
  作者：Fu-Li Xie、Yan Wang、Jian-Wei Zhu、Hui-Hua Xu、Qi-Feng Guo、Yong Wu、Si-Hong Liu

  DOI：10.1016/j.jinorgbio.2022.112011

  日期：2022.12

  blocked the cell cycle at the G0/G1 phase. Further studies revealed that complexes can increase intracellular reactive oxygen species (ROS) and Ca2+, which accompanied by mitochondria-mediated intrinsic apoptosis pathway. In addition, autophagy was also investigated. Taken together, the complexes induce HOS apoptosis through a ROS-mediated mitochondrial dysfunction pathway and inhibition of the PI3K (

  三铱(III)聚吡啶配合物[Ir(bzq) 2 (maip)](PF 6 ) ( Ir1 ， bzq = benzo[ h ]quinoline, maip = 3-aminophenyl-1H-imidazo[4,5-f][1 ,10]phenanthroline), [Ir(bzq) 2 (apip)](PF 6 ) ( Ir2 , api = 2-aminophenyl-1H-imidazo[4,5-f][1,10]phenanthroline) 和 [Ir( bzq) 2 (paip)](PF 6 ) ( Ir3, paip = 4-aminophenyl-1H-imidazo[4,5-f][1,10]phenanthroline) 被合成和表征。通过MTT（3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物）方法评估三种复合物对人骨肉瘤HOS、U2OS、MG63和正常LO2细胞的细胞毒活性。结果表明，Ir1
• Synthesis, characterization and anticancer activity of two Ru(II) polypyridyl complexes [Ru(dpq)2L](PF6)2 (L = maip, paip)
  作者：Shu-Fen He、Bing-Bing Chen、Ye-Hua Hao、Jia-Xi Chen、Xing-Dong Song、Jun Mei、Wen-Xiu Chen、Jing Sun

  DOI：10.1016/j.ica.2018.05.006

  日期：2018.8

  Two new Ru(II) polypyridyl complexes, [Ru(dpq)(2)(maip)](PF6)(2) (1) and [Ru(dpq)(2)(paip)](PF6)(2) (2) (dpq = dipyrido [3,2-d:2',3'-f]quinoxaline; maip = 2-(3-aminophenyl) imidazo[4,5-f][1,10] phenanthroline; paip = 2-(4-aminophenyl) imidazo[4,5-f][1,10] phenanthroline), were synthesized and characterized to investigate their antitumor activity. MTT assay showed that both complexes exhibit moderate antitumor activity against HeLa, A549, HepG2, MCF-7, and CNE-2 cell lines, but have lower cytotoxicity compared to cisplatin. Complex 1 exhibits higher toxicity than complex 2. Mechanism studies indicate that the two Ru(II) complexes were present in the cytoplasm after 10 h of incubation with HeLa cells and were selectively localized in the mitochondria. Additionally, the two complexes arrested the cell cycle in the G0/G1 phase, which suggests that both complexes can induce cancer cell death through reactive oxygen species (ROS)-dependent pathways. (C) 2018 Elsevier B.V. All rights reserved.
• Studies of ruthenium(II) polypyridyl complexes on cytotoxicity in vitro, apoptosis, DNA-binding and antioxidant activity
  作者：Hong-Liang Huang、Yun-Jun Liu、Cheng-Hui Zeng、Jun-Hua Yao、Zhen-Hua Liang、Zheng-Zheng Li、Fu-Hai Wu

  DOI：10.1016/j.molstruc.2009.12.026

  日期：2010.3

  Two new ruthenium(II) polypyridyl complexes [Ru(dmb)(2)(maip)](ClO4)(2) 1 (maip = 2-(3-aminophenyl)imizado[4,5-f][1,10]phenanthroline and [Ru(dmb)(2)(maip)](ClO4)(2) 2 (paip = 2-(4-aminophenyl)imidazo[4,5-f][1,10]phenanthroline, dmb = 4,4'-dimethyl-2,2'-bipyridine) have been synthesized and characterized. The DNA-binding behaviors of complexes I and 2 were studied by viscosity measurements, thermal denaturation, photocleavage, absorption titration and luminescence spectra. The results show that the two complexes intercalate between the base pairs of DNA. The DNA-binding constants K-b for complexes 1 and 2 were determined to be 1.12 +/- 0.11 x 10(5) M-1 (s = 2.17) and 3.46 +/- 0.59 x 10(5) M-1 (s = 2.11) M-1. The studies on the mechanism of photocleavage demonstrate that superoxide anion radical (O-2(center dot-)) and singlet oxygen (O-1(2)) may play an important role. The cytotoxicity of these complexes has been evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. The IC50 values are 19.21. 33.15, 38.57 and 21.15 for complex 1 and 41.77, 123.58, 255.44 and 49.11 for complex 2 against BEL-7402, C-6, HepG-2 and MCF-7 cell lines, respectively. The apoptosis assay was carried out with acridine orange/ethidium bromide (AO/EB) staining methods and the results indicate that complexes can induce the apoptosis of BEL-7402 cells. The experiments on antioxidant activity show these complexes exhibit good antioxidant activity against hydroxyl radical (OH center dot). Crown Copyright (C) 2009 Published by Elsevier B.V. All rights reserved.