4-cyano-1-(4-(2-fluorophenyl)piperazin-yl)-3-phenylpyrido[1,2-a]benzimidazole-8-carboxylic acid | 1309934-29-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-cyano-1-(4-(2-fluorophenyl)piperazin-yl)-3-phenylpyrido[1,2-a]benzimidazole-8-carboxylic acid
• 英文别名: 4-Cyano-1-[4-(2-fluorophenyl)piperazin-1-yl]-3-phenylpyrido[1,2-a]benzimidazole-8-carboxylic acid；4-cyano-1-[4-(2-fluorophenyl)piperazin-1-yl]-3-phenylpyrido[1,2-a]benzimidazole-8-carboxylic acid
• CAS: 1309934-29-9
• 化学式: C₂₉H₂₂FN₅O₂
• 分子量: 491.524
• InChiKey: DIHPAJGAYFGLAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  苯甲酰乙酸乙酯 在 ammonium acetate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 生成 4-cyano-1-(4-(2-fluorophenyl)piperazin-yl)-3-phenylpyrido[1,2-a]benzimidazole-8-carboxylic acid
  参考文献：
  名称：

  Synthesis of potential anticancer derivatives of pyrido[1,2-a]benzimidazoles

  摘要：

  In this study, the starting compounds, 2-cyanomethyl benzimidazoles (1 or 2) were reacted with ethyl acetoacetate, ethyl benzoylacetate, or 2-acetylbutyrolactone to give the novel series of 4-cyano-3-substituted-1-oxo-1H, 5H-pyrido[1,2-a]benzimidazole (3-6, 15, 16). The latter was chlorinated to give compounds 7-10, 17, 18 then aminated with 4-(2-fluorophenyl) piperazine to afford compounds 11-14, 19, 20. The structures of the new compounds were confirmed by elemental analysis as well as H-1-NMR, IR, and mass data. All the synthesized products were subjected to in vitro anticancer screening that revealed that all the tested compounds exhibited antitumor activity against human breast adenocarcinoma (MCF7) cell line, with IC50's 3.43-14.70 mu g/ml.

  DOI：

  10.1007/s00044-011-9636-y

文献信息

• Synthesis of potential anticancer derivatives of pyrido[1,2-a]benzimidazoles
  作者：Hanan M. Refaat

  DOI：10.1007/s00044-011-9636-y

  日期：2012.7

  In this study, the starting compounds, 2-cyanomethyl benzimidazoles (1 or 2) were reacted with ethyl acetoacetate, ethyl benzoylacetate, or 2-acetylbutyrolactone to give the novel series of 4-cyano-3-substituted-1-oxo-1H, 5H-pyrido[1,2-a]benzimidazole (3-6, 15, 16). The latter was chlorinated to give compounds 7-10, 17, 18 then aminated with 4-(2-fluorophenyl) piperazine to afford compounds 11-14, 19, 20. The structures of the new compounds were confirmed by elemental analysis as well as H-1-NMR, IR, and mass data. All the synthesized products were subjected to in vitro anticancer screening that revealed that all the tested compounds exhibited antitumor activity against human breast adenocarcinoma (MCF7) cell line, with IC50's 3.43-14.70 mu g/ml.