5-(N,N-diethylamino)benzimidazo[1,2-a]quinoline-6-carbonitrile | 1612162-06-7

• 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: 5-(N,N-diethylamino)benzimidazo[1,2-a]quinoline-6-carbonitrile
• 英文别名: 5-(Diethylamino)benzimidazolo[1,2-a]quinoline-6-carbonitrile；5-(diethylamino)benzimidazolo[1,2-a]quinoline-6-carbonitrile
• CAS: 1612162-06-7
• 化学式: C₂₀H₁₈N₄
• 分子量: 314.39
• InChiKey: IRDWUPYYLBFITH-UHFFFAOYSA-N

物化性质

• 熔点：
  160-162 °C
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氰甲基苯并咪唑 在 吡啶 、 五氯化磷 、 potassium tert-butylate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 170.0 ℃ 、4.0 MPa 条件下， 反应 10.0h， 生成 5-(N,N-diethylamino)benzimidazo[1,2-a]quinoline-6-carbonitrile
  参考文献：
  名称：

  Synthesis, antiproliferative activity and DNA binding properties of novel 5-Aminobenzimidazo[1,2-a]quinoline-6-carbonitriles

  摘要：

  The synthesis of 5-amino substituted benzimidazo[1,2-a]quinolines prepared by microwave assisted amination from halogeno substituted precursor was described. The majority of compounds were active at micromolar concentrations against colon, lung and breast carcinoma cell lines in vitro. The N,N-dimethylaminopropyl 9 and piperazinyl substituted derivative 19 showed the most pronounced activity towards all of the three tested tumor cell lines, which could be correlated to the presence of another N heteroatom and its potential interactions with biological targets. The DNA binding studies, consisting of UV/Visible absorbency, melting temperature studies, and fluorescence and circular dichroism titrations, revealed that compounds 9, 19 and 20 bind to DNA as strong intercalators. The cellular distribution analysis, based on compounds' intrinsic fluorescence, showed that compound 20 does not enter the cell, while compounds 9 and 19 do, which is in agreement with their cytotoxic effects. Compound 9 efficiently targets the nucleus whereas 19, which also showed DNA intercalating properties in vitro, was mostly localised in the cytoplasm suggesting that the antitumor mechanism of action is DNA-independent.

  DOI：

  10.1016/j.ejmech.2014.04.049

文献信息

• Synthesis, antiproliferative activity and DNA binding properties of novel 5-Aminobenzimidazo[1,2-a]quinoline-6-carbonitriles
  作者：Nataša Perin、Raja Nhili、Katja Ester、William Laine、Grace Karminski-Zamola、Marijeta Kralj、Marie-Hélène David-Cordonnier、Marijana Hranjec

  DOI：10.1016/j.ejmech.2014.04.049

  日期：2014.6

  The synthesis of 5-amino substituted benzimidazo[1,2-a]quinolines prepared by microwave assisted amination from halogeno substituted precursor was described. The majority of compounds were active at micromolar concentrations against colon, lung and breast carcinoma cell lines in vitro. The N,N-dimethylaminopropyl 9 and piperazinyl substituted derivative 19 showed the most pronounced activity towards all of the three tested tumor cell lines, which could be correlated to the presence of another N heteroatom and its potential interactions with biological targets. The DNA binding studies, consisting of UV/Visible absorbency, melting temperature studies, and fluorescence and circular dichroism titrations, revealed that compounds 9, 19 and 20 bind to DNA as strong intercalators. The cellular distribution analysis, based on compounds' intrinsic fluorescence, showed that compound 20 does not enter the cell, while compounds 9 and 19 do, which is in agreement with their cytotoxic effects. Compound 9 efficiently targets the nucleus whereas 19, which also showed DNA intercalating properties in vitro, was mostly localised in the cytoplasm suggesting that the antitumor mechanism of action is DNA-independent.