4-((4-chloro-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)oxy)benzonitrile | 1609280-32-1

• 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-((4-chloro-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)oxy)benzonitrile
• 英文别名: 4-(4-Chloro-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yloxy)benzonitrile；4-[[4-chloro-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl]oxy]benzonitrile
• CAS: 1609280-32-1
• 化学式: C₁₅H₁₅ClN₆O
• 分子量: 330.777
• InChiKey: XHZYQXPOZJEIHV-UHFFFAOYSA-N

物化性质

• 熔点：
  217-219 °C
• 沸点：
  542.9±60.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-((4-chloro-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)oxy)benzonitrile 在 potassium phosphate 、 palladium diacetate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 13.0h， 生成 (Z)-4-((4-(4-(4-chlorobenzylideneamino)phenyl)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)oxy)benzonitrile
  参考文献：
  名称：

  Facile synthesis of benzonitrile/nicotinonitrile based s-triazines as new potential antimycobacterial agents

  摘要：

  A common strategy to synthesize 4/6-(4-(4-methylpiperazin-1-yl)-6-(4-(4-oxo-2-phenylthiazolidin-3-yl)phenyl)-1,3,5-triazin-2-yloxy)benzonitriles/nicotinonitriles was developed by applying an efficient palladium-catalyzed C-C Suzuki coupling. Moreover, the synthesized compounds were also tested for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv using BACTEC MGIT and Lowenstein-Jensen MIC methods. Several compounds displayed profound antimycobacterial activity in combination with low toxicity towards mammalian cells. The best results were observed amongst the nicotinonitrile substituted s-triazine analogs and it could be a potential starting point to develop new lead compounds in the fight against M. tuberculosis H(37)Rv. The newly synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.085
• 作为产物：
  描述：

  N-甲基哌嗪 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 4-((4-chloro-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)oxy)benzonitrile
  参考文献：
  名称：

  Facile synthesis of benzonitrile/nicotinonitrile based s-triazines as new potential antimycobacterial agents

  摘要：

  A common strategy to synthesize 4/6-(4-(4-methylpiperazin-1-yl)-6-(4-(4-oxo-2-phenylthiazolidin-3-yl)phenyl)-1,3,5-triazin-2-yloxy)benzonitriles/nicotinonitriles was developed by applying an efficient palladium-catalyzed C-C Suzuki coupling. Moreover, the synthesized compounds were also tested for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv using BACTEC MGIT and Lowenstein-Jensen MIC methods. Several compounds displayed profound antimycobacterial activity in combination with low toxicity towards mammalian cells. The best results were observed amongst the nicotinonitrile substituted s-triazine analogs and it could be a potential starting point to develop new lead compounds in the fight against M. tuberculosis H(37)Rv. The newly synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.085