6-chloro-N-[2-(trifluoromethyl)phenyl]pyrazine-2-carboxamide | 938075-10-6

• 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: 6-chloro-N-[2-(trifluoromethyl)phenyl]pyrazine-2-carboxamide
• CAS: 938075-10-6
• 化学式: C₁₂H₇ClF₃N₃O
• 分子量: 301.655
• InChiKey: JBGYSBZNIHTORI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-氯-吡嗪羰酰氯(9ci) 、 邻氨基三氟甲苯 以 吡啶 、 丙酮 为溶剂， 反应 0.5h， 生成 6-chloro-N-[2-(trifluoromethyl)phenyl]pyrazine-2-carboxamide
  参考文献：
  名称：

  Synthesis and antimycobacterial evaluation of substituted pyrazinecarboxamides

  摘要：

  Unsubstituted, halogenated and/or alkylated pyrazine-2-carboxylic acid amides connected via -CONH- bridge with substituted anilines were synthesized using currently known synthetic pathways. The synthetic approach, analytical, spectroscopic, lipophilicity and biological data of 20 newly synthesized compounds are presented. Structure-activity relationships among the chemical structures, the antimycobacterial, antifungal, photosynthesis inhibiting and antialgal activity of the evaluated substituted N-phenylpyrazine-2-carboxamides are discussed. 5-tert-Butyl-6-chloro-N-(3-trifluoromethylphenyl)pyrazine-2-carboxamide (19) has shown the highest activity against Mycobacterium tuberculosis H(37)Rv (MIC = 3.13 mu g/mL). The highest antifungal effect against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for N-(3-trifluoromethylphenyl)pyrazine-2-carboxamide (14, MIC = 62.5 mu mol/mL). The highest reduction of chlorophyll content in Chlorella vulgaris was found for pyrazine-2-carboxylic acid (3-trifluoromethylphenyl)amide (9, IC50 = 12.1 mu mol/L). (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.07.013

文献信息

• Synthesis and antimycobacterial evaluation of substituted pyrazinecarboxamides
  作者：Martin Dolezal、Pavlina Cmedlova、Lukas Palek、Jarmila Vinsova、Jiri Kunes、Vladimir Buchta、Josef Jampilek、Katarina Kralova

  DOI：10.1016/j.ejmech.2007.07.013

  日期：2008.5

  Unsubstituted, halogenated and/or alkylated pyrazine-2-carboxylic acid amides connected via -CONH- bridge with substituted anilines were synthesized using currently known synthetic pathways. The synthetic approach, analytical, spectroscopic, lipophilicity and biological data of 20 newly synthesized compounds are presented. Structure-activity relationships among the chemical structures, the antimycobacterial, antifungal, photosynthesis inhibiting and antialgal activity of the evaluated substituted N-phenylpyrazine-2-carboxamides are discussed. 5-tert-Butyl-6-chloro-N-(3-trifluoromethylphenyl)pyrazine-2-carboxamide (19) has shown the highest activity against Mycobacterium tuberculosis H(37)Rv (MIC = 3.13 mu g/mL). The highest antifungal effect against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for N-(3-trifluoromethylphenyl)pyrazine-2-carboxamide (14, MIC = 62.5 mu mol/mL). The highest reduction of chlorophyll content in Chlorella vulgaris was found for pyrazine-2-carboxylic acid (3-trifluoromethylphenyl)amide (9, IC50 = 12.1 mu mol/L). (C) 2007 Elsevier Masson SAS. All rights reserved.