1-(4-methylphenyl)-3-methyl-5-(4-methylphenylthio)-4-pyrazolaldoxime-(5-chloro-3-methyl-1-(4-methylphenyl)pyrazol-4-ylmethyl ether) | 1083082-46-5

• 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-(4-methylphenyl)-3-methyl-5-(4-methylphenylthio)-4-pyrazolaldoxime-(5-chloro-3-methyl-1-(4-methylphenyl)pyrazol-4-ylmethyl ether)
• 英文别名: N-[[5-chloro-3-methyl-1-(4-methylphenyl)pyrazol-4-yl]methoxy]-1-[3-methyl-1-(4-methylphenyl)-5-(4-methylphenyl)sulfanylpyrazol-4-yl]methanimine
• CAS: 1083082-46-5
• 化学式: C₃₁H₃₀ClN₅OS
• 分子量: 556.131
• InChiKey: KPEXWGVFEKLBBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  82.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  C₁₂H₁₂Cl₂N₂ 、 N-[[3-methyl-1-(4-methylphenyl)-5-(4-methylphenyl)sulfanylpyrazol-4-yl]methylidene]hydroxylamine 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.34h， 以55%的产率得到1-(4-methylphenyl)-3-methyl-5-(4-methylphenylthio)-4-pyrazolaldoxime-(5-chloro-3-methyl-1-(4-methylphenyl)pyrazol-4-ylmethyl ether)
  参考文献：
  名称：

  Synthesis and Antiviral Activities of Pyrazole Derivatives Containing an Oxime Moiety

  摘要：

  Target compounds 4a-n were obtained by the reaction of 1-substituted phenyl-3-methyl-5-substituted phenylthio-4-pyrazolaidoximes (3) with chloromethylated heterocyclic compounds (CICH2-R-3) under reflux conditions in ethanol. Subsequently, the oxidation of 4a-e with KMnO4 in HOAc at room temperature afforded eight new compounds, 5a-h. The synthesized compounds were characterized by physical constants, and the structures of the title compounds were confirmed by IR, H-1 NMR, C-13 NMR, and elemental analysis. The bioassay revealed that the compounds possessed antiviral activities. It was found that title compounds 4a and 4g had the same inactivation effects against TMV (EC50 = 58.7 and 65.3 mu g/mL) as the commercial product Ningnanmycin (EC50 = 52.7 mu g/mL). To the best of our knowledge, this is the first report on the antiviral activity of pyrazole derivatives containing an oxime moiety.

  DOI：

  10.1021/jf802489e