3-nitro-benzimidazo[1,2-a]quinoline | 1345044-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-nitro-benzimidazo[1,2-a]quinoline
• 英文别名: 3-Nitrobenzimidazolo[1,2-a]quinoline
• CAS: 1345044-22-5
• 化学式: C₁₅H₉N₃O₂
• 分子量: 263.255
• InChiKey: OPYOXUVTRDODDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-nitro-benzimidazo[1,2-a]quinoline 在 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 3-amino-benzimidazo[1,2-a]quinoline hydrochloride
  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 在 polyphosphoric acid 作用下， 以 环丁砜 为溶剂， 反应 4.5h， 生成 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

文献信息

• 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.