4-(2-bromoacetyl)-5-methyl-N,1-diphenyl-pyrazole-3-carboxamide | 1028561-23-0

• 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: 4-(2-bromoacetyl)-5-methyl-N,1-diphenyl-pyrazole-3-carboxamide
• 英文别名: 4-(2-bromoacetyl)-5-methyl-N,1-diphenylpyrazole-3-carboxamide
• CAS: 1028561-23-0
• 化学式: C₁₉H₁₆BrN₃O₂
• 分子量: 398.259
• InChiKey: MUIMJLNASYOVTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-bromoacetyl)-5-methyl-N,1-diphenyl-pyrazole-3-carboxamide 、 邻苯二胺 以 乙醇 为溶剂， 反应 1.0h， 以87%的产率得到5-methyl-N,1-diphenyl-4-quinoxalin-2-ylpyrazole-3-carboxamide
  参考文献：
  名称：

  Synthesis of new N-phenylpyrazole derivatives with potent antimicrobial activity

  摘要：

  The versatile synthons 4-(2-bromoacetyl)-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole ( 3) and 4-[( E)-3-(dimethylamino) acryloyl]-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole ( 2) were used as precursors for the synthesis of a series of phenylpyrazoles with different aromatic ring systems at position 4. The antimicrobiological evaluation of the newly synthesized compounds was carried out in vitro assays for antifungal and antibacterial activities. Amongst the tested compounds, 4-acetyl-5methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (1), 4-[( E)-3-(dimethylamino) acryloyl]-5-methyl-1-phenyl-3-phenylcarbamoyl-1H- pyrazole (2),4-(2-bromoacetyl)-5-methyl-1-phenyl-3-phenylcarbamoyl-1H- pyrazole (3) and 4-(2-aminothiazol-4-yl)-5-methyl-1-phenyl-3-phenylcarbamoyl-1H- pyrazole ( 17) showed interesting antimicrobial properties. In particular, all tested compounds produced inhibitory effects against pathogenic yeast (Candida albicans) similar or superior to those of reference drug. In addition, compound 3 showed excellent activity against pathogenic mould ( Aspergillus). From structure-activity relationship (SAR) point of view, the attachment of bromoacetyl moiety to pyrazole ring can be considered as a breakthrough in developing a new therapeutic antifungal agent related to phenylpyrazole system. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.043
• 作为产物：
  描述：

  4-acetyl-5-methyl-1-phenyl-1H-pyrazole-3-carboxylic acid anilide 在 溴 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以78%的产率得到4-(2-bromoacetyl)-5-methyl-N,1-diphenyl-pyrazole-3-carboxamide
  参考文献：
  名称：

  Synthesis of new N-phenylpyrazole derivatives with potent antimicrobial activity

  摘要：

  The versatile synthons 4-(2-bromoacetyl)-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole ( 3) and 4-[( E)-3-(dimethylamino) acryloyl]-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole ( 2) were used as precursors for the synthesis of a series of phenylpyrazoles with different aromatic ring systems at position 4. The antimicrobiological evaluation of the newly synthesized compounds was carried out in vitro assays for antifungal and antibacterial activities. Amongst the tested compounds, 4-acetyl-5methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (1), 4-[( E)-3-(dimethylamino) acryloyl]-5-methyl-1-phenyl-3-phenylcarbamoyl-1H- pyrazole (2),4-(2-bromoacetyl)-5-methyl-1-phenyl-3-phenylcarbamoyl-1H- pyrazole (3) and 4-(2-aminothiazol-4-yl)-5-methyl-1-phenyl-3-phenylcarbamoyl-1H- pyrazole ( 17) showed interesting antimicrobial properties. In particular, all tested compounds produced inhibitory effects against pathogenic yeast (Candida albicans) similar or superior to those of reference drug. In addition, compound 3 showed excellent activity against pathogenic mould ( Aspergillus). From structure-activity relationship (SAR) point of view, the attachment of bromoacetyl moiety to pyrazole ring can be considered as a breakthrough in developing a new therapeutic antifungal agent related to phenylpyrazole system. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.043