1-benzofuran-2-yl(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)methanone | 1310487-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzofuran-2-yl(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)methanone
• CAS: 1310487-77-4
• 化学式: C₁₉H₁₄N₂O₃
• 分子量: 318.332
• InChiKey: XKGIZZPSAWSUMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  68.26
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  水杨醛 、 4-(2-chloroacetyl)-5-methyl-2-phenyl-1H-pyrazol-3-one 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以85%的产率得到1-benzofuran-2-yl(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)methanone
  参考文献：
  名称：

  Synthesis and antimicrobial activity of some new 4-hetarylpyrazole and furo[2,3-c]pyrazole derivatives

  摘要：

  In continuation of our efforts to find a new class of antimicrobial agents, a series of 4-hetarylpyrazoles and furo[2,3-c]pyrazoles were prepared via the reaction of 2-chloro-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)ethanone ( 1) with an appropriate nucleophilic reagents. These compounds were screened for their antibacterial activity against Gram-positive bacteria (Bacillus subtilis and Bacillus thuringiensis), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) and antifungal activity against Fusarium oxysporum and Botrytis fabae. Among the synthesized compounds, 1-(5-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazole-4-yl)-2-methylfuran-3-yl)ethanone (12) showed equal activity with chloramphenicol against B. subtilis (MIC 3.125 mu g/mL), while its activity was 50% lower than of chloramphenicol against B. thuringiensis. N-[(4Z)-3-Methyl-1-phenyl-1H-furo[2,3-c]pyrazol-4(5H)-ylidene]-1H-benzimidazol-2-amine (7) and 2-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-4H-furo [3,2-c]chromen-4-one (13) were found to exhibit the most potent in vitro antifungal activity with MICs (6.25 mu g/mL) against B. fabae and F. oxysporum. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.045