4-(2-fluorophenyl)-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole-2-amine | 380334-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-(2-fluorophenyl)-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole-2-amine
• 英文别名: 2-amino-4-(2'-fluorophenyl)-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole；4-(2-fluorophenyl)-4,10-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-2-amine
• CAS: 380334-97-4
• 化学式: C₁₅H₁₂FN₅
• 分子量: 281.292
• InChiKey: UWUAOLUTMCQGNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-fluorophenyl)-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole-2-amine 、 乙氧基甲叉丙二酸二乙酯 以 N,N-二甲基甲酰胺 为溶剂， 以68%的产率得到ethyl 6-(2-fluorophenyl)-4-oxo-4,6-dihydro-1(12)(13)H-pyrimido[2',1':4,5][1,3,5]triazino[1,2-a]benzimidazole-3-carboxylate
  参考文献：
  名称：

  乙基6-芳基-4-氧代-4,6-二氢-1（12）（13）h-嘧啶基-[2'，1'：4,5] [1,3,5]三嗪[1， 2- a ]苯并咪唑-3-羧酸盐†

  摘要：

  乙基6-芳基-4-氧代-4,6-二氢-1（12）（13）H-嘧啶基[2'，1'：4,5] [1,3,5]三嗪[1， 2-一个] -苯并咪唑-3-羧酸盐（4A-p ）中描述通过嘧啶环环至4-芳基-3,4-二氢[1,3,5]三嗪并[1,2一]苯并咪唑-2-由2-胍基苯并咪唑（1）获得的胺（2a-p）。使用核磁共振光谱研究了所制备化合物中的互变异构现象。发现化合物2a-p主要以3,4-二氢互变异构形式存在于二甲基亚砜溶液中。化合物4a-p以1-，12-和13 H的动态平衡存在-形式。发现4a-d的甲基化仅导致13-甲基取代的衍生物9a-d。

  DOI：

  10.1002/jhet.5570430614
• 作为产物：
  描述：

  2-胍基苯并咪唑 、 2-氟苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以90%的产率得到4-(2-fluorophenyl)-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole-2-amine
  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.
• Synthesis of ethyl 6-aryl-4-oxo-4,6-dihydro-1(12)(13)<i>h</i>-pyrimido-[2′,1′:4,5][1,3,5]triazino[1,2-<i>a</i>]benzimidazole-3-carboxylates
  作者：Anton V. Dolzhenko、Wai-Keung Chui、Anna V. Dolzhenko

  DOI：10.1002/jhet.5570430614

  日期：2006.11

  The synthesis of ethyl 6-aryl-4-oxo-4,6-dihdro-1(12)(13)H-pyrimido[2′,1′:4,5][1,3,5]triazino[1,2-a]-benzimidazole-3-carboxylates (4a-p) was described via pyrimidine ring annulation to 4-aryl-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole-2-amines (2a-p) which were obtained from 2-guanidinobenzimidazole (1). Tautomerism in the prepared compounds was investigated using nmr spectroscopy. Compounds 2a-p

  乙基6-芳基-4-氧代-4,6-二氢-1（12）（13）H-嘧啶基[2'，1'：4,5] [1,3,5]三嗪[1， 2-一个] -苯并咪唑-3-羧酸盐（4A-p ）中描述通过嘧啶环环至4-芳基-3,4-二氢[1,3,5]三嗪并[1,2一]苯并咪唑-2-由2-胍基苯并咪唑（1）获得的胺（2a-p）。使用核磁共振光谱研究了所制备化合物中的互变异构现象。发现化合物2a-p主要以3,4-二氢互变异构形式存在于二甲基亚砜溶液中。化合物4a-p以1-，12-和13 H的动态平衡存在-形式。发现4a-d的甲基化仅导致13-甲基取代的衍生物9a-d。