N-(4-hydroxy-3,5-dimethylphenyl)-2-(1-iso-propyl-1H-indazol-3-yl)-acetamide | 1408237-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: N-(4-hydroxy-3,5-dimethylphenyl)-2-(1-iso-propyl-1H-indazol-3-yl)-acetamide
• 英文别名: N-(4-hydroxy-3,5-dimethylphenyl)-2-(1-propan-2-ylindazol-3-yl)acetamide
• CAS: 1408237-72-8
• 化学式: C₂₀H₂₃N₃O₂
• 分子量: 337.422
• InChiKey: XEKPJQKASWUPAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(1H-吲唑-3-基)乙酸甲酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 水 、 caesium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 N-(4-hydroxy-3,5-dimethylphenyl)-2-(1-iso-propyl-1H-indazol-3-yl)-acetamide
  参考文献：
  名称：

  DPPH radical scavenging activity of paracetamol analogues

  摘要：

  Biochemical studies suggest a direct relationship between the radical scavenging activity of paracetamol (I) and its antipyretic and analgesic action. To evaluate the effect of chemical modifications on the radical scavenging activity of compounds of type I, analogues 1-14 were prepared and submitted to a stable free radical (DPPH; 1,1-diphenyl-2-picryl-hydrazyl) assay. All paracetamol derivatives showed a significant higher efficiency than the parent compound. This study showed that radical scavenging activity can be increased by decreasing the phenolic ortho substituents steric hindrance or by introducing substituents on the acyl moiety like an indazole ring or the ionic N-methyl morpholinium group. A significant activating effect was also observed by replacing the 1,4-acylamidophenol with a 1,4-acylamidonaphthol system. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.098

文献信息

• DPPH radical scavenging activity of paracetamol analogues
  作者：Maria Alessandra Alisi、Mario Brufani、Nicola Cazzolla、Francesca Ceccacci、Patrizia Dragone、Marco Felici、Guido Furlotti、Barbara Garofalo、Angela La Bella、Osvaldo Lanzalunga、Francesca Leonelli、Rinaldo Marini Bettolo、Caterina Maugeri、Luisa Maria Migneco、Vincenzo Russo

  DOI：10.1016/j.tet.2012.09.098

  日期：2012.12

  Biochemical studies suggest a direct relationship between the radical scavenging activity of paracetamol (I) and its antipyretic and analgesic action. To evaluate the effect of chemical modifications on the radical scavenging activity of compounds of type I, analogues 1-14 were prepared and submitted to a stable free radical (DPPH; 1,1-diphenyl-2-picryl-hydrazyl) assay. All paracetamol derivatives showed a significant higher efficiency than the parent compound. This study showed that radical scavenging activity can be increased by decreasing the phenolic ortho substituents steric hindrance or by introducing substituents on the acyl moiety like an indazole ring or the ionic N-methyl morpholinium group. A significant activating effect was also observed by replacing the 1,4-acylamidophenol with a 1,4-acylamidonaphthol system. (C) 2012 Elsevier Ltd. All rights reserved.