(2E)-3-(5-chloro-3-methyl-1-phenylpyrazol-4-yl)-1-(1,3-dimethyl-2,4,6-pyrimidinetrione-5-yl)-2-propen-1-one | 1309596-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2E)-3-(5-chloro-3-methyl-1-phenylpyrazol-4-yl)-1-(1,3-dimethyl-2,4,6-pyrimidinetrione-5-yl)-2-propen-1-one
• 英文别名: 5-[(E)-3-(5-chloro-3-methyl-1-phenylpyrazol-4-yl)prop-2-enoyl]-1,3-dimethyl-1,3-diazinane-2,4,6-trione
• CAS: 1309596-53-9
• 化学式: C₁₉H₁₇ClN₄O₄
• 分子量: 400.821
• InChiKey: PCMLNSJPJGKFTN-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  92.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E)-3-(5-chloro-3-methyl-1-phenylpyrazol-4-yl)-1-(1,3-dimethyl-2,4,6-pyrimidinetrione-5-yl)-2-propen-1-one 在 肼 作用下， 反应 0.08h， 以89%的产率得到5-[5-(5-chloro-3-methyl-1-phenylpyrazol-4-yl)-4,5-dihydro-1H-pyrazol-3-yl]-1,3-dimethyl-1,3-diazinane-2,4,6-trione
  参考文献：
  名称：

  Thermal solvent-free synthesis of novel pyrazolyl chalcones and pyrazolines as potential antimicrobial agents

  摘要：

  A novel approach was adopted for the synthesis of series of new pyrazolyl chalcones (3a-c) by the reaction of 5-chloro-3-methyl-1-phenylpyrazole-4-carboxaldehyde (1) with different 5-acetylbarbituric acid derivatives (2a-c) under thermal solvent-free condition. The chalcones were then converted to the corresponding pyrazolines (4a-c) under the same condition in excellent yields. All the synthesized compounds were characterized using elemental analysis and spectral data (IR, H-1 NMR, and mass spectrometry). The synthesized compounds were tested for their antimicrobial activity by disk diffusion assay with slight modifications against Gram-positive, Gram-negative strains of bacteria as well as fungal strains. The investigation of antimicrobial screening revealed that compounds (3a-4c) showed good antibacterial and antifungal activities, respectively. Among the screened compounds, 3b showed more potent inhibitory activity (MIC = 12.5 mu g/ml) nearly to that of standard antibiotics ciprofloxacin, griseofulvin and fluconazole. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.080
• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 在 三氯氧磷 作用下， 反应 0.17h， 生成 (2E)-3-(5-chloro-3-methyl-1-phenylpyrazol-4-yl)-1-(1,3-dimethyl-2,4,6-pyrimidinetrione-5-yl)-2-propen-1-one
  参考文献：
  名称：

  Thermal solvent-free synthesis of novel pyrazolyl chalcones and pyrazolines as potential antimicrobial agents

  摘要：

  A novel approach was adopted for the synthesis of series of new pyrazolyl chalcones (3a-c) by the reaction of 5-chloro-3-methyl-1-phenylpyrazole-4-carboxaldehyde (1) with different 5-acetylbarbituric acid derivatives (2a-c) under thermal solvent-free condition. The chalcones were then converted to the corresponding pyrazolines (4a-c) under the same condition in excellent yields. All the synthesized compounds were characterized using elemental analysis and spectral data (IR, H-1 NMR, and mass spectrometry). The synthesized compounds were tested for their antimicrobial activity by disk diffusion assay with slight modifications against Gram-positive, Gram-negative strains of bacteria as well as fungal strains. The investigation of antimicrobial screening revealed that compounds (3a-4c) showed good antibacterial and antifungal activities, respectively. Among the screened compounds, 3b showed more potent inhibitory activity (MIC = 12.5 mu g/ml) nearly to that of standard antibiotics ciprofloxacin, griseofulvin and fluconazole. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.080