2-amino-4-[3',5'-bis(trifluoromethyl)phenyl]-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-amino-4-[3',5'-bis(trifluoromethyl)phenyl]-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole
• 英文别名: 4-[3,5-Bis(trifluoromethyl)phenyl]-1,4-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-2-amine；4-[3,5-bis(trifluoromethyl)phenyl]-1,4-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-2-amine
• 化学式: C₁₇H₁₁F₆N₅
• 分子量: 399.298
• InChiKey: QUCXGLDENPDRMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-胍基苯并咪唑 、 3,5-双三氟甲基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以65%的产率得到2-amino-4-[3',5'-bis(trifluoromethyl)phenyl]-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole
  参考文献：
  名称：

  Synthesis and biological activity of fluorinated 2-amino-4-aryl-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazoles

  摘要：

  The heterocyclic nucleus s-triazino[1,2-a]benzimidazole has been reported to exhibit antibacterial activity. In this study, seven new 3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole derivatives were prepared via cyclocondensation between 2-guanidinobenzimidazole and fluorine substituted (including trifluoromethyl) benzaldehydes. The structures of all the compounds were confirmed by H-1, C-13 NMR and IR spectral data. Spectral data also suggested the existence of various tautomeric forms of the fluorine-containing s-triazino[1,2-a]benzimidazole compounds. The synthesized compounds were also screened for antibacterial and bovine dihydrofolate reductase (DHFR) inhibitory activities. The compound 3g substituted with a 3',5-bis(trifluoromethyl)phenyl moiety demonstrated the best antibacterial activity in the series. None of the tested compounds significantly inhibited bovine DHFR. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.02.009

文献信息

• Synthesis and biological activity of fluorinated 2-amino-4-aryl-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazoles
  作者：Anton V. Dolzhenko、Wai-Keung Chui、Anna V. Dolzhenko、Lai-Wah Chan

  DOI：10.1016/j.jfluchem.2005.02.009

  日期：2005.5

  The heterocyclic nucleus s-triazino[1,2-a]benzimidazole has been reported to exhibit antibacterial activity. In this study, seven new 3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole derivatives were prepared via cyclocondensation between 2-guanidinobenzimidazole and fluorine substituted (including trifluoromethyl) benzaldehydes. The structures of all the compounds were confirmed by H-1, C-13 NMR and IR spectral data. Spectral data also suggested the existence of various tautomeric forms of the fluorine-containing s-triazino[1,2-a]benzimidazole compounds. The synthesized compounds were also screened for antibacterial and bovine dihydrofolate reductase (DHFR) inhibitory activities. The compound 3g substituted with a 3',5-bis(trifluoromethyl)phenyl moiety demonstrated the best antibacterial activity in the series. None of the tested compounds significantly inhibited bovine DHFR. (c) 2005 Elsevier B.V. All rights reserved.