(E)-2-(2-chloro-5-nitrostyryl)benzimidazole | 141838-80-4

• 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: (E)-2-(2-chloro-5-nitrostyryl)benzimidazole
• 英文别名: 2-[(E)-2-(2-chloro-5-nitrophenyl)-ethenyl]benzimidazole；2-[(E)-2-(2-chloro-5-nitrophenyl)ethenyl]-1H-benzimidazole
• CAS: 141838-80-4
• 化学式: C₁₅H₁₀ClN₃O₂
• 分子量: 299.716
• InChiKey: LGDCPIQGHFBSKU-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-chloro-5-nitrostyryl)benzimidazole 以 环丁砜 为溶剂， 反应 1.5h， 以95%的产率得到3-nitro-benzimidazo[1,2-a]quinoline
  参考文献：
  名称：

  Novel biologically active nitro and amino substituted benzimidazo[1,2-a]quinolines

  摘要：

  This manuscript described the synthesis and biological activity of novel nitro substituted E-2-styryl-benzimidazoles and E-2-(2-benzimidazolyl)-3-phenylacrylonitriles and nitro and amino substituted benzimidazo[1,2-a]quinolines (4-5, 6-11, 17-20, and 21-32). All of the compounds showed significant growth inhibitory effect towards five tumor cell lines, whereby the IC(50) concentrations of 11, 20, 28, 29, 30, 32 are in the low micromolar range (IC(50) = 2-19 mu M). The DNA binding experiments did not show significant affinity of two selected compounds towards ct-DNA. The flow cytometry analysis of potential cell cycle perturbations after the treatment with compounds 9, 11, 25, and 29 demonstrated that all of the compounds (5 mu M approximate to IC(50)) significantly delayed the progression through G1 phase, as demonstrated by the accumulation of cells in G1 phase, accompanied with the reduction of the cell number in the cells in S phase, which does not point to DNA damage as the main mechanism of action. Also, fluorescence microscopy study showed cytoplasmic distribution of the compounds, demonstrating that DNA is not the primary target of compounds. Thus, considerable antiproliferative effects of studied compounds are due to interactions with other biological targets within cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.002
• 作为产物：
  描述：

  2-氯-5-硝基肉桂酸 、 邻苯二胺 在 polyphosphoric acid 作用下， 反应 3.0h， 以51%的产率得到(E)-2-(2-chloro-5-nitrostyryl)benzimidazole
  参考文献：
  名称：

  Novel biologically active nitro and amino substituted benzimidazo[1,2-a]quinolines

  摘要：

  This manuscript described the synthesis and biological activity of novel nitro substituted E-2-styryl-benzimidazoles and E-2-(2-benzimidazolyl)-3-phenylacrylonitriles and nitro and amino substituted benzimidazo[1,2-a]quinolines (4-5, 6-11, 17-20, and 21-32). All of the compounds showed significant growth inhibitory effect towards five tumor cell lines, whereby the IC(50) concentrations of 11, 20, 28, 29, 30, 32 are in the low micromolar range (IC(50) = 2-19 mu M). The DNA binding experiments did not show significant affinity of two selected compounds towards ct-DNA. The flow cytometry analysis of potential cell cycle perturbations after the treatment with compounds 9, 11, 25, and 29 demonstrated that all of the compounds (5 mu M approximate to IC(50)) significantly delayed the progression through G1 phase, as demonstrated by the accumulation of cells in G1 phase, accompanied with the reduction of the cell number in the cells in S phase, which does not point to DNA damage as the main mechanism of action. Also, fluorescence microscopy study showed cytoplasmic distribution of the compounds, demonstrating that DNA is not the primary target of compounds. Thus, considerable antiproliferative effects of studied compounds are due to interactions with other biological targets within cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.002

文献信息

• FLUORESCENT CELLULAR MARKERS
  申请人：Zayas Beatriz

  公开号：US20100256378A1

  公开（公告）日：2010-10-07

  A synthesis procedure for benzazolo[3,2-a]quinolinium chloride salts and the inclusion of amino-substituent and nitro-substituent resulting in four compounds such as NBQ-38(7-Ethyl-3-nitrobenzimidazolo[3,2-a]quinolinium Chloride), NBQ-95(2-Chloro-10-methyl-3-nitrobenzothiazolo[3,2-a]quinolinium chloride), ABQ-38(3-amino-7-ethylbenzimidazo[3,2-a]quinolinium chloride), and ABQ-95(3-amino-2-chloro-10-methylbenzothiazolo[3,2-a]quinolinium chloride) wherein said procedures provides an increment in the compounds biological activity. The compounds are further used for intra cellular binding, cytotoxicity on malignant cells through apoptosis activation mediated by mitochondrial damage and caspases 3 and 7 activation, cellular organelles binding and damage, and a marker due to the auto-fluorescent properties.

  一种合成苯并咔唑[3,2-a]喹啉盐酸盐的方法，包括引入氨基取代基和硝基取代基，从而得到四种化合物，分别为NBQ-38（7-乙基-3-硝基苯并咪唑[3,2-a]喹啉盐酸盐），NBQ-95（2-氯-10-甲基-3-硝基苯并噻唑[3,2-a]喹啉盐酸盐），ABQ-38（3-氨基-7-乙基苯并咪唑[3,2-a]喹啉盐酸盐）和ABQ-95（3-氨基-2-氯-10-甲基苯并噻唑[3,2-a]喹啉盐酸盐）。该方法提高了化合物的生物活性。这些化合物进一步用于细胞内结合、通过线粒体损伤和caspases 3和7激活介导的凋亡激活对恶性细胞的细胞毒性、细胞器结合和损伤以及由于自荧光特性而产生的标记。
• Synthesis and characterization of new platinum(II) complexes containing thiazole and imidazole donors III. Dichlorobis(styrylbenzazole)platinum(II) complexes
  作者：Mariel M. Muir、Osvaldo Cox、Luis A. Rivera、Mayra E. Cadiz、Eulalia Medina

  DOI：10.1016/s0020-1693(00)80339-4

  日期：1992.1

  Platinum(II) complexes of the type cis-[Pt(L)2Cl2], where L is a styrylbenzazole, have been prepared. The benzazoles included derivatives of imidazole, thiazole and oxazole. The ligands and the complexes were characterized by their melting points, elemental analyses, NMR, UV-Vis and IR spectra. The benzazole ligands are all coordinated to the Pt through N. The assignment of cis geometry for the complexes was based on the method of synthesis, comparison with a styrylbenzazole complex of known geometry, and far-IR spectral data.
• US8124770B2
  申请人：——

  公开号：US8124770B2

  公开（公告）日：2012-02-28
• Novel biologically active nitro and amino substituted benzimidazo[1,2-a]quinolines
  作者：Nataša Perin、Lidija Uzelac、Ivo Piantanida、Grace Karminski-Zamola、Marijeta Kralj、Marijana Hranjec

  DOI：10.1016/j.bmc.2011.09.002

  日期：2011.11

  This manuscript described the synthesis and biological activity of novel nitro substituted E-2-styryl-benzimidazoles and E-2-(2-benzimidazolyl)-3-phenylacrylonitriles and nitro and amino substituted benzimidazo[1,2-a]quinolines (4-5, 6-11, 17-20, and 21-32). All of the compounds showed significant growth inhibitory effect towards five tumor cell lines, whereby the IC(50) concentrations of 11, 20, 28, 29, 30, 32 are in the low micromolar range (IC(50) = 2-19 mu M). The DNA binding experiments did not show significant affinity of two selected compounds towards ct-DNA. The flow cytometry analysis of potential cell cycle perturbations after the treatment with compounds 9, 11, 25, and 29 demonstrated that all of the compounds (5 mu M approximate to IC(50)) significantly delayed the progression through G1 phase, as demonstrated by the accumulation of cells in G1 phase, accompanied with the reduction of the cell number in the cells in S phase, which does not point to DNA damage as the main mechanism of action. Also, fluorescence microscopy study showed cytoplasmic distribution of the compounds, demonstrating that DNA is not the primary target of compounds. Thus, considerable antiproliferative effects of studied compounds are due to interactions with other biological targets within cells. (C) 2011 Elsevier Ltd. All rights reserved.