4-((4-(4-(2-(4-methoxyphenyl)-4-oxothiazolidin-4-oneolidin-3-yl)phenyl)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)oxy)benzonitrile | 1609280-56-9

• 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-((4-(4-(2-(4-methoxyphenyl)-4-oxothiazolidin-4-oneolidin-3-yl)phenyl)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)oxy)benzonitrile
• 英文别名: 4-[[4-[4-[2-(4-Methoxyphenyl)-4-oxo-thiazolidin-3-yl]phenyl]-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl]oxy]benzonitrile；4-[[4-[4-[2-(4-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]phenyl]-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl]oxy]benzonitrile
• CAS: 1609280-56-9
• 化学式: C₃₁H₂₉N₇O₃S
• 分子量: 579.682
• InChiKey: GSDQBGXTDXVFRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  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-methoxyphenyl)-4-oxothiazolidin-4-oneolidin-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

文献信息

• Facile synthesis of benzonitrile/nicotinonitrile based s-triazines as new potential antimycobacterial agents
  作者：Amit B. Patel、Kishor H. Chikhalia、Premlata Kumari

  DOI：10.1016/j.ejmech.2014.03.085

  日期：2014.5

  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.