4-[(2,4-dichlorophenyl)(2-hydroxy-1-naphthyl)methyl]-2-(4-fluorophenyl)-5-methyl-2,3-dihydro-1H-pyrazol-3-one | 1334395-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[(2,4-dichlorophenyl)(2-hydroxy-1-naphthyl)methyl]-2-(4-fluorophenyl)-5-methyl-2,3-dihydro-1H-pyrazol-3-one
• 英文别名: 4-[(2,4-dichlorophenyl)-(2-hydroxy-1-naphthyl)methyl]-2-(4-fluorophenyl)-5-methyl-1H-pyrazol-3-one；4-[(2,4-dichlorophenyl)-(2-hydroxynaphthalen-1-yl)methyl]-2-(4-fluorophenyl)-5-methyl-1H-pyrazol-3-one
• CAS: 1334395-23-1
• 化学式: C₂₇H₁₉Cl₂FN₂O₂
• 分子量: 493.364
• InChiKey: TYFKUZDGZDCLDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二氯苯甲醛 、 乙酰乙酸甲酯 、 4-氟苯肼 、 2-萘酚 在 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 4.0h， 以65%的产率得到4-[(2,4-dichlorophenyl)(2-hydroxy-1-naphthyl)methyl]-2-(4-fluorophenyl)-5-methyl-2,3-dihydro-1H-pyrazol-3-one
  参考文献：
  名称：

  A facile four-component sequential protocol in the expedient synthesis of novel 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones in water and their antitubercular evaluation

  摘要：

  A series of 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones has been synthesized by one-pot, four-component sequential reactions of phenylhydrazine, methyl acetoacetate, aromatic aldehydes and beta-naphthol in the presence of p-toluenesulphonic acid in water in good yields. These 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones were screened for in-vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) using agar dilution method. Among the 15 compounds screened, 4-[(2,4-dichlorophenyl)(2-hydroxy-1-naphthyl)methyl]-2-(4-fluorophenyl)-5-methyl-2,3-dihydro-1H-3-pyrazolone displays the maximum potency with a minimum inhibitory concentration (MIC) of 1.6 mu M against MTB, being 2.94 and 4.75 times more active than ciprofloxacin and ethambutol respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.029