4-[(E)-3-(dimethylamino)prop-2-enoyl]-5-methyl-N,1-diphenylpyrazole-3-carboxamide | 1028561-21-8

• 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-[(E)-3-(dimethylamino)prop-2-enoyl]-5-methyl-N,1-diphenylpyrazole-3-carboxamide
• CAS: 1028561-21-8
• 化学式: C₂₂H₂₂N₄O₂
• 分子量: 374.442
• InChiKey: YRPZMMPFQZOCDT-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(E)-3-(dimethylamino)prop-2-enoyl]-5-methyl-N,1-diphenylpyrazole-3-carboxamide 在 乙酸铵 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以88%的产率得到5-methyl-4-(1,2-oxazol-3-yl)-N,1-diphenylpyrazole-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：

  N,N-二甲基甲酰胺二甲基缩醛 、 4-acetyl-5-methyl-1-phenyl-1H-pyrazole-3-carboxylic acid anilide 以 xylene 为溶剂， 生成 4-[(E)-3-(dimethylamino)prop-2-enoyl]-5-methyl-N,1-diphenylpyrazole-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

文献信息

• Regioselective synthesis and antitumor screening of some novel N-phenylpyrazole derivatives
  作者：Ahmad M. Farag、Abdelrahman S. Mayhoub、Saber E. Barakat、Ashraf H. Bayomi

  DOI：10.1016/j.bmc.2007.10.015

  日期：2008.1

  The versatile, hitherto unreported 4-acetyl-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (3) was prepared via the reaction of 2-(2-phenylhydrazono)-2-chloro-N-phenylacetamide with pentan-2,4-dione in the presence of sodium ethoxide. Reaction of 3 with dimethylformamide-dimethylacetal (DMF-DMA) furnished the corresponding 4-[(E)-3-(dimethylamino)aci-yloyl]-5-methyl-1-phenyl-3-phenylcarbamoyl-1H-pyrazole (5). The latter product underwent regioselective 1,3-dipolar cycloaddition with some nitrilimines to afford the non-isolable dihydropyrazole intermediates which then lose dimethylamine yielding the corresponding pyrazole derivatives. The preliminary screening for the antitumor activity of all newly synthesized compounds was carried out against Ehrlich Ascites Carcinoma tumor cells. (C) 2007 Elsevier Ltd. All rights reserved.