5-oxo-6-cyanobenzimidazolo<1,2-a>quinoline | 109924-68-7

• 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-oxo-6-cyanobenzimidazolo<1,2-a>quinoline
• 英文别名: 5-ketobenzimidazo[1,2-a]quinoline-6-carbonitrile；5-oxo-5,7-dihydrobenzimidazo[1,2-a]quinoline-6-carbonitrile；5-oxo-7H-benzimidazolo[1,2-a]quinoline-6-carbonitrile
• CAS: 109924-68-7
• 化学式: C₁₆H₉N₃O
• 分子量: 259.267
• InChiKey: MFUDWLYZGFUXJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  56.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-oxo-6-cyanobenzimidazolo<1,2-a>quinoline 在 五氯化磷 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 170.0 ℃ 、4.0 MPa 条件下， 反应 5.0h， 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
• 作为产物：
  描述：

  2-氰甲基苯并咪唑 在 吡啶 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-oxo-6-cyanobenzimidazolo<1,2-a>quinoline
  参考文献：
  名称：

  氨基取代的苯并咪唑并[1,2- a ]喹啉类化合物：抗增殖能力，3D QSAR研究和DNA结合特性

  摘要：

  我们描述了一系列2-氨基，5-氨基和2,5-二氨基取代的苯并咪唑并[1,2- a ]喹啉的合成，3D衍生的定量结构-活性关系（QSAR），抗增殖活性和DNA结合特性由环保的未催化微波辅助胺化制得。体外评估抗增殖活性针对结肠，肺和乳腺癌细胞系；活性范围从亚微摩尔到微摩尔。2-氨基取代的类似物证明了最强的抗增殖活性，而5-氨基和或2,5-二氨基取代的衍生物的活性却低得多。带有4-甲基-或3,5-二甲基-1-哌嗪基取代基的衍生物是最活跃的。使用熔融温度研究，一系列光谱研究（UV / Visible，荧光和圆二色性）和生化实验研究了本文制备的选定取代的苯并咪唑并[1,2- a ]喹啉的DNA结合特性和相互作用方式。拓扑异构酶I介导的DNA松弛和DNase I足迹实验）。都复合36它的双季碘盐37插在DNA螺旋的相邻碱基对之间，而化合物33的拓扑异构酶I毒性很弱。进行了3D-QSAR分析，以鉴定氢键

  DOI：

  10.1016/j.ejmech.2016.07.007

文献信息

• Amino substituted benzimidazo[1,2- a ]quinolines: Antiproliferative potency, 3D QSAR study and DNA binding properties
  作者：Nataša Perin、Raja Nhili、Maja Cindrić、Branimir Bertoša、Darko Vušak、Irena Martin-Kleiner、William Laine、Grace Karminski-Zamola、Marijeta Kralj、Marie-Hélène David-Cordonnier、Marijana Hranjec

  DOI：10.1016/j.ejmech.2016.07.007

  日期：2016.10

  We describe the synthesis, 3D-derived quantitative structure-activity relationship (QSAR), antiproliferative activity and DNA binding properties of a series of 2-amino, 5-amino and 2,5-diamino substituted benzimidazo[1,2-a]quinolines prepared by environmentally friendly uncatalyzed microwave assisted amination. The antiproliferative activities were assessed in vitro against colon, lung and breast carcinoma

  我们描述了一系列2-氨基，5-氨基和2,5-二氨基取代的苯并咪唑并[1,2- a ]喹啉的合成，3D衍生的定量结构-活性关系（QSAR），抗增殖活性和DNA结合特性由环保的未催化微波辅助胺化制得。体外评估抗增殖活性针对结肠，肺和乳腺癌细胞系；活性范围从亚微摩尔到微摩尔。2-氨基取代的类似物证明了最强的抗增殖活性，而5-氨基和或2,5-二氨基取代的衍生物的活性却低得多。带有4-甲基-或3,5-二甲基-1-哌嗪基取代基的衍生物是最活跃的。使用熔融温度研究，一系列光谱研究（UV / Visible，荧光和圆二色性）和生化实验研究了本文制备的选定取代的苯并咪唑并[1,2- a ]喹啉的DNA结合特性和相互作用方式。拓扑异构酶I介导的DNA松弛和DNase I足迹实验）。都复合36它的双季碘盐37插在DNA螺旋的相邻碱基对之间，而化合物33的拓扑异构酶I毒性很弱。进行了3D-QSAR分析，以鉴定氢键
• Antimicrobial activity of derivatives of benzimidazolo[1,2-a]quinolines
  作者：F. S. Babichev、V. K. Patratii、Yu. M. Volovenko、N. G. Prodanchuk、V. G. Sinchenko、A. G. Nemazanyi、T. A. Silaeva

  DOI：10.1007/bf00764663

  日期：1989.7
• VOLOVENKO YU. M.; NEMAZANYJ A. G.; VESELSKAYA G. L.; TYUXTENKO S. I.; BAB+, DOKL. AN YCCP,(1986) N 12, 30-33
  作者：VOLOVENKO YU. M.、 NEMAZANYJ A. G.、 VESELSKAYA G. L.、 TYUXTENKO S. I.、 BAB+

  DOI：——

  日期：——
• NOVEL COMPOSITIONS, USES AND METHODS FOR MAKING THEM
  申请人：Pimera, Inc.

  公开号：US20210094952A1

  公开（公告）日：2021-04-01

  Generally, the present invention provides novel quinolone compounds and pharmaceutical composition thereof which may inhibit cell proliferation and/or induce cell apoptosis. The present invention also provides methods of preparing such compounds and compositions, and methods of making and using the same.
• 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.