4-((4-(4-aminophenyl)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)oxy)benzonitrile | 1609280-34-3

• 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-(4-aminophenyl)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)oxy)benzonitrile
• 英文别名: 4-{[4-[4-Aminophenyl]-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl]oxy}benzonitrile；4-[[4-(4-aminophenyl)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl]oxy]benzonitrile
• CAS: 1609280-34-3
• 化学式: C₂₁H₂₁N₇O
• 分子量: 387.444
• InChiKey: MHLQEQAXNHEDGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-((4-(4-aminophenyl)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)oxy)benzonitrile 在 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 生成 4-((4-(4-(2-(4-bromophenyl)-4-oxothiazolidin-3-yl)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 phosphate 、 palladium diacetate 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 31.0h， 生成 4-((4-(4-aminophenyl)-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