3-nitro-benzimidazo[1,2-a]quinoline-6-carbonitrile | 664327-70-2

• 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-6-carbonitrile
• 英文别名: 3-nitro-6-cyano-benzimidazo[1,2-a]quinoline；Benzimidazo[1,2-a]quinoline-6-carbonitrile, 3-nitro-；3-nitrobenzimidazolo[1,2-a]quinoline-6-carbonitrile
• CAS: 664327-70-2
• 化学式: C₁₆H₈N₄O₂
• mdl: MFCD06618609
• 分子量: 288.265
• InChiKey: BEGOIWGBIIJBQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 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：
  86.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-nitro-benzimidazo[1,2-a]quinoline-6-carbonitrile 在 盐酸 、 tin(II) chloride dihdyrate 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以67%的产率得到3-amino-6-cyano-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-硝基苯甲醛 在 哌啶 作用下， 以 环丁砜 、 乙醇 为溶剂， 反应 4.0h， 生成 3-nitro-benzimidazo[1,2-a]quinoline-6-carbonitrile
  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

• Synthesis of Aza-Fused Polycyclic Quinolines through Copper-Catalyzed Cascade Reactions
  作者：Qian Cai、Zhengqiu Li、Jiajia Wei、Liangbin Fu、Chengyong Ha、Duanqing Pei、Ke Ding

  DOI：10.1021/ol1002225

  日期：2010.4.2

  the synthesis of aza-fused polycyclic quinolines (e.g., benzimidazo[1,2-a]quinolines) is described. This protocol includes an intermolecular condensation followed by a copper-catalyzed intramolecular C−N coupling reaction. The method is applied to a wide range of 2-iodo, 2-bromo, and 2-chloro aryl aldehyde substrates to yield the aza-fused polycyclic quinolines in good yields.

  描述了一种合成氮杂稠合多环喹啉（例如，苯并咪唑并[1,2- a ]喹啉）的新的有效方法。该方案包括分子间缩合，然后进行铜催化的分子内CN偶联反应。该方法适用于广泛的2-碘，2-溴和2-氯芳基醛底物，从而以良好的收率生产出氮杂稠合的多环喹啉。
• The <i>tert</i>-Amino Effect in the Synthesis of Hetaryl- and Arylsulfonyl-Substituted Pyrrolo- and Pyrido[1,2-<i>a</i>]quinoline Derivatives and their Pyrazolo Annulated Analogues
  作者：Anton Tverdokhlebov、Alexander Gorulya、Andrey Tolmachev、Alexander Kostyuk、Alexander Chernega、Eduard Rusanov

  DOI：10.1055/s-2005-870004

  日期：——

  cyclization of the corresponding arylidene derivatives. Similarly, starting from 2-(l-piperidinyl)benzaldehydes 5-hetaryl and 5-tosyl-2,3,4,4a,5,6-hexahydro-1H-pyrido[l,2-a]qumoline-5-carbonitriles were obtained. For the hetaryl-substituted derivatives the cyclization step was found to be assisted by protons. In addition 4,5,5a,6,7,8-hexahydro-1H-pyrazolo[3,4-e]indolizine and l,4,5,5a,6,7,8,9-octahydro-pyrazolo[4

  4-杂芳基和4-甲苯磺酰基-1,2,3,3a,4,5-六氢吡咯并[1,2-a]喹啉-4-甲腈通过2-(l-吡咯烷基)苯甲醛的缩合反应分两步制备与取代的乙腈 XCH 2 CN (X = 杂芳基，甲苯磺酰基)，然后热环化相应的亚芳基衍生物。类似地，从 2-(l-哌啶基)苯甲醛开始，5-杂芳基和 5-甲苯磺酰基-2,3,4,4a,5,6-hexahydro-1H-pyrido[l,2-a]qumoline-5-carbonitriles获得。对于杂芳基取代的衍生物，发现环化步骤由质子辅助。此外还有4,5,5a,6,7,8-六氢-1H-吡唑并[3,4-e]中氮茚和l,4,5,5a,6,7,8,9-八氢-吡唑[4, 3-c]喹啉衍生物通过相同的方法从5-(1-吡咯烷基)-和5-(1-哌啶基)-3-甲基-1-苯基吡唑-4-甲醛开始制备。
• 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.