N'-[(E)-(4-hydroxy-3-methoxyphenyl)methylidene]-4-methyl-1,5-diphenyl-1H-pyrazole-3-carbohydrazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N'-[(E)-(4-hydroxy-3-methoxyphenyl)methylidene]-4-methyl-1,5-diphenyl-1H-pyrazole-3-carbohydrazide
• 英文别名: N-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]-4-methyl-1,5-diphenylpyrazole-3-carboxamide
• 化学式: C₂₅H₂₂N₄O₃
• 分子量: 426.475
• InChiKey: VUTWDTNPJGKDBX-WGOQTCKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  88.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 4-methyl-1,5-diphenyl-1H-pyrazole-3-carboxylate 在 氯化亚砜 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 24.0h， 生成 N'-[(E)-(4-hydroxy-3-methoxyphenyl)methylidene]-4-methyl-1,5-diphenyl-1H-pyrazole-3-carbohydrazide
  参考文献：
  名称：

  1,5-Diarylpyrazole and vanillin hybrids: Synthesis, biological activity and DFT studies

  摘要：

  Herein, we report the design and synthesis of 13 diarylpyrazole hybrids with vanillin constructed as dual compounds against oxidative stress and diabetes. Compounds were tested in two different antioxidant assays. It was found that all compounds showed an important antioxidant activity in both DPPH and ORAC models and the activity was even more remarkable than vanillin. In addition, the hypoglycemic effect of compounds 1, 2, 4 and 12 was evaluated. Interestingly, compound 1 had the most potent hypoglycemic effect with a glycemia reduction of 71%, which was higher than rimonabant. Finally, a DFT study to propose a reasonable antioxidant mechanism is detailed. Both thermodynamic and kinetic studies indicated that the most feasible mechanism consists in the HAT abstraction of the phenolic hydrogen due to the formation of an stable transition state through the most rapid and exergonic path, while the SPLET mechanism is the most significant at higher pH values. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.010