5-(4-hydroxybenzoyl)pyrazine-2-carboxamide | 677020-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-hydroxybenzoyl)pyrazine-2-carboxamide
• CAS: 677020-92-7
• 化学式: C₁₂H₉N₃O₃
• 分子量: 243.222
• InChiKey: BUOAJOAZAYYSRB-UHFFFAOYSA-N

物化性质

• 熔点：
  235-236 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  544.5±50.0 °C(Predicted)
• 密度：
  1.421±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-hydroxybenzoyl)pyrazine-2-carboxamide 在 ammonium sulfide 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 5-(4-Hydroxybenzoyl)pyrazine-2-carbothioamide
  参考文献：
  名称：

  Substituted 5-aroylpyrazine-2-carboxylic acid derivatives: synthesis and biological activity

  摘要：

  Homolytic aroylation of pyrazine nucleus with various substituted aromatic carbaldehydes afforded a series of 5-aroylpyrazine-2-carboxylic acid derivatives. The synthetic approach, analytical and spectroscopic data of all compounds synthesized, their preliminary in vitro evaluation of antituberculotic and antifungal activities, cytotoxicity data and subsequent SAR studies are presented. Among all derivatives prepared, only 5-(4-chlorobenzoyl)-pyrazine-2-carbothioamide (3d) showed promising activity (90% inhibition) against Mycobacterium tuberculosis. The highest antifungal effect (MIC<1.95 microM ml(-1)) against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 5-benzoylpyrazine-2-carbothioamide (3a). Thioamides exhibited higher in vitro antimicrobial activity than the corresponding amides.

  DOI：

  10.1016/s0014-827x(03)00163-0
• 作为产物：
  描述：

  吡嗪酰胺 、 对羟基苯甲醛 在 iron(II) sulfate 叔丁基过氧化氢 、 硫酸 、 溶剂黄146 作用下， 反应 2.0h， 以11%的产率得到5-(4-hydroxybenzoyl)pyrazine-2-carboxamide
  参考文献：
  名称：

  Substituted 5-aroylpyrazine-2-carboxylic acid derivatives: synthesis and biological activity

  摘要：

  Homolytic aroylation of pyrazine nucleus with various substituted aromatic carbaldehydes afforded a series of 5-aroylpyrazine-2-carboxylic acid derivatives. The synthetic approach, analytical and spectroscopic data of all compounds synthesized, their preliminary in vitro evaluation of antituberculotic and antifungal activities, cytotoxicity data and subsequent SAR studies are presented. Among all derivatives prepared, only 5-(4-chlorobenzoyl)-pyrazine-2-carbothioamide (3d) showed promising activity (90% inhibition) against Mycobacterium tuberculosis. The highest antifungal effect (MIC<1.95 microM ml(-1)) against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 5-benzoylpyrazine-2-carbothioamide (3a). Thioamides exhibited higher in vitro antimicrobial activity than the corresponding amides.

  DOI：

  10.1016/s0014-827x(03)00163-0

文献信息

• Synthesis, characterization and molecular structure of Ru(II) complex with benzoylpyrazine carboxylic acid derivatives
  作者：J.G. Małecki、A. Maroń、M. Serda、M. Dolezal、J. Polański

  DOI：10.1016/j.poly.2012.04.033

  日期：2012.6

  Two benzoylpyrazine ligands containing carboxyl and amide functions and their hydride-carbonyl complexes of ruthenium were synthesized and characterized by infrared, proton, carbon phosphorus nuclear magnetic resonance, electronic absorption and emission spectroscopy and X-ray crystallography. The experimental studies were completed by theoretical calculations. From the electronic spectrum of the complex the Racah's and nepheloauxetic parameters are calculated. The electronic structure of the complexes, presented in particular by the density of states diagram, have been correlated with its ability to fluoresce and used to analyze the UV-Vis spectra. (c) 2012 Elsevier Ltd. All rights reserved.