1H-Imidazo[4,5-f][1,10]phenanthroline, 2-(2,4-dichlorophenyl)- | 1304515-56-7

• 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: 1H-Imidazo[4,5-f][1,10]phenanthroline, 2-(2,4-dichlorophenyl)-
• 英文别名: (2-(2,4-dichlorophenyl)-1H-imidazo[4,5-f]-[1,10]phenanthroline)；(2-(2,4-dichlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline)；2-(2,4-dichlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline
• CAS: 1304515-56-7
• 化学式: C₁₉H₁₀Cl₂N₄
• 分子量: 365.221
• InChiKey: IQPYFXUJASGESQ-UHFFFAOYSA-N

物化性质

• 沸点：
  642.8±65.0 °C(Predicted)
• 密度：
  1.528±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 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：

  硫酸锰水合物 、 间苯二甲酸 、 1H-Imidazo[4,5-f][1,10]phenanthroline, 2-(2,4-dichlorophenyl)- 在 sodium hydroxide 作用下， 以 水 为溶剂， 以78%的产率得到[Mn(2-(2,4-dichlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline)(isophthalic acid)₃]n
  参考文献：
  名称：

  Syntheses, crystal structures, and photophysical properties of two 2-D coordination polymers

  摘要：

  Two coordination polymers, [Mn(dipt)(m-BDC)3] n (1) and [Pb(mip)(1,4-NDC)] n (2) [dipt?=?2-(2,4-dichlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline, mip?=?2-(3-methoxyphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline, m-BDC?=?isophthalic acid, 1,4-NDC?=?naphthalene-1,4-dicarboxylic acid], have been synthesized by hydrothermal reactions and characterized by elemental analysis, thermogravimetric analysis, infrared spectrum, and single-crystal X-ray diffraction. Single-crystal X-ray diffraction reveals that 1 and 2 have 1-D chain architecture. Complex 1 has a 2-D-layered structure constructed from CH center dot center dot center dot O hydrogen bonds. Complex 2 has a 2-D-layered structure constructed from NH center dot center dot center dot O hydrogen bonds and pp interactions. TG analyses suggest 1 and 2 have excellent thermal stabilities from hydrogen bonds and pp interactions. Mn(II) in 1 has trigonal bipyramidal geometry surrounded by three carboxylate oxygen atoms from three monodentate bridging m-BDC and two nitrogen atoms from one dipt. Pb(II) has [:PbN2O4] pentagonal bipyramidal geometry in 2. The luminescent properties for dipt, mip, 1, and 2 are also presented.

  DOI：

  10.1080/00958972.2012.740022
• 作为产物：
  描述：

  1,10-菲罗啉 在 硫酸 、 ammonium acetate 、 硝酸 作用下， 以 溶剂黄146 为溶剂， 生成 1H-Imidazo[4,5-f][1,10]phenanthroline, 2-(2,4-dichlorophenyl)-
  参考文献：
  名称：

  Syntheses, crystal structures, and photophysical properties of two 2-D coordination polymers

  摘要：

  Two coordination polymers, [Mn(dipt)(m-BDC)3] n (1) and [Pb(mip)(1,4-NDC)] n (2) [dipt?=?2-(2,4-dichlorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline, mip?=?2-(3-methoxyphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline, m-BDC?=?isophthalic acid, 1,4-NDC?=?naphthalene-1,4-dicarboxylic acid], have been synthesized by hydrothermal reactions and characterized by elemental analysis, thermogravimetric analysis, infrared spectrum, and single-crystal X-ray diffraction. Single-crystal X-ray diffraction reveals that 1 and 2 have 1-D chain architecture. Complex 1 has a 2-D-layered structure constructed from CH center dot center dot center dot O hydrogen bonds. Complex 2 has a 2-D-layered structure constructed from NH center dot center dot center dot O hydrogen bonds and pp interactions. TG analyses suggest 1 and 2 have excellent thermal stabilities from hydrogen bonds and pp interactions. Mn(II) in 1 has trigonal bipyramidal geometry surrounded by three carboxylate oxygen atoms from three monodentate bridging m-BDC and two nitrogen atoms from one dipt. Pb(II) has [:PbN2O4] pentagonal bipyramidal geometry in 2. The luminescent properties for dipt, mip, 1, and 2 are also presented.

  DOI：

  10.1080/00958972.2012.740022

文献信息

• A novel Co(II) based multifunctional metal-organic framework: Synthesis, fluorescence sensing and magnetic analysis
  作者：Han-yang Sun、Zi-run Wang、Xue Li、Shuang Han、Jia-jun Wang、Wen-fang Li、Chun-ling Liu、Chuan-bi Li

  DOI：10.1016/j.ica.2018.11.028

  日期：2019.2

  -1H-imidazo [4,5–f]-[1,10]phenanthroline, HPClA = 3-(2-chlorophenyl)acrylie) has been synthesized under solvothermal conditions and structurally characterized by elemental analysis, IR spectroscopy, single-crystal X-ray diffraction analysis, nitrogen adsorption analysis and powder X-ray diffraction. NCl-1 constructed by six coordinated mode with metal center and connected different ligands and ions, exhibits

  摘要一种新的配位Co（II）配合物，即[Co2（DIPT）4（PClA）2Cl2]·H2O（NCl-1）（DIPT = 2-（2,4-二氯苯基）-1H-咪唑[4,5 –f]-[1,10]菲咯啉，HPClA = 3-（2-氯苯基）丙烯酸，是在溶剂热条件下合成的，并通过元素分析，红外光谱，单晶X射线衍射分析，氮吸附分析对结构进行表征和粉末X射线衍射。NCl-1由六种配位模式与金属中心构成，并连接不同的配体和离子，在氢键和π-π堆积相互作用的作用下呈现三维结构。发光探测表明，NCl-1对有机溶剂（MeOH）和金属离子（Fe3 +）表现出高度的选择性和敏感性。此外，
• 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。
• Crystal structure, thermal behavior, luminescence and theoretical calculation of a new Pb(II) coordination complex
  作者：He Wang、Shuang Han、Linan Dun、Baosheng Zhang、Xue Chen、Jiajun Wang、Chuanbi Li、Chunling Liu

  DOI：10.1016/j.molstruc.2020.128950

  日期：2020.12

  this report, a new coordination complex Pb(CDIPT)2(L)2 (CDIPT= 10‑chloro‑2-(2,4-dichlorophenyl)-1H-imidazo[4,5-f]-[1,10]phenanthroline, HL= 2,4-dichlorophenyl acrylic acid) has been synthesized and fully characterized by elemental analysis, IR spectroscopy, UV spectrum, single-crystal X-ray diffraction analysis, luminescence spectra, TGA and powder X-ray diffraction. The structural analysis showed that

  摘要 在本报告中，一种新的配位络合物 Pb(CDIPT)2(L)2 (CDIPT= 10-chloro-2-(2,4-dichlorophenyl)-1H-imidazo[4,5-f]-[1,10 ]菲咯啉，HL= 2,4-二氯苯基丙烯酸）已合成并通过元素分析、红外光谱、紫外光谱、单晶 X 射线衍射分析、发光光谱、TGA 和粉末 X 射线衍射进行了充分表征。结构分析表明配合物1是具有七个配位Pb(II)离子的零维结构。此外，相邻的复杂单元通过氢键 [N(4)-H(4)•••O(4) 和 N(7)-H(7)•••O 扩展成二维超分子网络(1)]。发光探索表明配合物1具有良好的光学性质。此外，量子化学计算是用 Gaussian09 程序进行的。
• Synthesis, DNA-binding, and antitumor activity of polypyridyl-ruthenium(II) complexes [Ru(L)₂(DClPIP)] (L = bpy, phen; DClPIP = 2-(2,4-dichlorophenyl)-1<i>H</i>-imidazo[4,5-<i>f</i>][1, 10]phenanthroline)
  作者：Shouhai Guan、Tao Pan、Yanyang Zhang、Zhaolin Zeng、Luwen Mu、Duo Zhu、Boyang Chang、Kangdi Zheng、Jiesheng Qian、Qiang Xie、Wenjie Mei、Wenjie Tang、Mingjun Bai

  DOI：10.1080/00958972.2019.1630614

  日期：2019.6.18

  Abstract Two new ruthenium(II) complexes, [Ru(bpy)2(DClPIP)](ClO4)2 (1) and [Ru(phen)2(DClPIP)](ClO4)2 (2) (bpy = 2,2′-bipyridine, phen = 1,10-phenanthroline, and DClPIP = 2-(2,4-dichlorophenyl)-1H-imidazo[4,5-f][1, 10]phenanthroline), have been prepared in high yield by using microwave-assisted synthesis technology. The anticancer activity of the two ruthenium(II) complexes against A549, C6, CNE-1

  摘要 两种新的钌 (II) 配合物 [Ru(bpy)2(DClPIP)](ClO4)2 (1) 和 [Ru(phen)2(DClPIP)]( )2 (2) (bpy = 2,2 '-联吡啶、phen = 1,10-菲咯啉和 DClPIP = 2-(2,4-二氯苯基)-1H-咪唑并[4,5-f][1, 10]菲咯啉)，已通过以下方法以高产率制备采用微波辅助合成技术。两种钌（II）配合物对 A549、C6、CNE-1 和 MDA-MB-231 细胞系的抗癌活性已通过 MTT 测定进行评估，结果表明 2 对所有选定的肿瘤细胞表现出比 1 更高的抗肿瘤活性线。此外，A549 细胞系对两种钌 (II) 复合物都敏感，尤其是对 2 (IC50 = 8.01 ± 0.36 μM)。同时，2对MCF-10A人正常细胞表现出低毒性。此外，通过电子吸收滴定、发光光谱、圆二色光谱和粘度测量研究了两种新的钌
• Two 2D metal–organic frameworks based on N-heterocyclic and polycarboxylates ligands: Syntheses, structures, and photoluminescent properties
  作者：Li Yan、Chuanbi Li、Dongsheng Zhu

  DOI：10.1016/j.molstruc.2012.08.017

  日期：2013.2

  Two novel complexes constructed from aromatic acid and N-heterocyclic ligands have been synthesized by hydrothermal reaction: [Mn(dipt)(BDC)(3)center dot H2O](n) (1) [dipt = 2-(2,4-dichloropheny1)-1H-imidazo[4,5-f] [1,10]phenanthroline, BDC = terephthalic acid] and [Pb(dnpt)(BDC)(2)](n) (2) [dnpt = 2-(4-nitrophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline]. Complexes 1 and 2 were characterized by elemental analysis, IR, single crystal X-ray diffraction and thermogravimetric analysis (TGA). The results suggest that complexes 1-2 exhibit 1D chain structure. The intermolecular C-H center dot center dot center dot O and N-H center dot center dot center dot O interactions extend the complexes into 2D networks, and the existing H-bonds further stabilized the title complexes, which can be proved by TGA experiment. Furthermore, the solid-state fluorescence spectrum of complexes 1 and 2 were also investigated, as well as the ligands dipt and dnpt. (C) 2012 Elsevier B.V. All rights reserved.