4-(5-甲基-1H-咪唑)苯酚 | 68337-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(5-甲基-1H-咪唑)苯酚
• 英文名称: 1-(4-hydroxyphenyl)-5-methylimidazole
• 英文别名: 4-(5-methyl-imidazol-1-yl)-phenol；4-(5-Methyl-1H-imidazol-1-YL)phenol；4-(5-methylimidazol-1-yl)phenol
• CAS: 68337-62-2
• 化学式: C₁₀H₁₀N₂O
• mdl: MFCD09038092
• 分子量: 174.202
• InChiKey: STZDOOANZJZCRW-UHFFFAOYSA-N

物化性质

• 沸点：
  362.6±25.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-碘丁烷 、 4-(5-甲基-1H-咪唑)苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以56%的产率得到1-(4-Butoxy-phenyl)-4-methyl-1H-imidazole
  参考文献：
  名称：

  Pyrazole and Isoxazole Derivatives as New, Potent, and Selective 20-Hydroxy-5,8,11,14-eicosatetraenoic Acid Synthase Inhibitors

  摘要：

  In a previous paper, we reported the N-hydroxyformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor. Despite its attraction as a potential therapeutic agent for cerebral diseases, the preparation of an injectable formulation of HET0016 was limited by its poor solubility under neutral conditions and instability under acidic conditions. The instability of HET0016 in acidic conditions is due to the N-hydroxyformamidine moiety, which is considered to be essential for the potent and selective activity seen in our previous study. The activity was maintained when the N-hydroxyformamidine moiety was replaced by an imidazole ring (3a; IC50 = 5.7 +/- 1.0 nM), but this was associated with a loss of selectivity for cytochrome P450s (CYPs). However, other azole derivatives such as isoxazole derivative 23 (IC50 value 38 +/- 10 nM) and pyrazole derivative 24 (IC50 value 23 +/- 12 nM) showed potent and selective activities with improved stability.

  DOI：

  10.1021/jm020557k
• 作为产物：
  描述：

  4-甲基咪唑 、 4-甲氧基苯硼酸 在 di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] chloride 、 氧气 、 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以7%的产率得到4-(5-甲基-1H-咪唑)苯酚
  参考文献：
  名称：

  Pyrazole and Isoxazole Derivatives as New, Potent, and Selective 20-Hydroxy-5,8,11,14-eicosatetraenoic Acid Synthase Inhibitors

  摘要：

  In a previous paper, we reported the N-hydroxyformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor. Despite its attraction as a potential therapeutic agent for cerebral diseases, the preparation of an injectable formulation of HET0016 was limited by its poor solubility under neutral conditions and instability under acidic conditions. The instability of HET0016 in acidic conditions is due to the N-hydroxyformamidine moiety, which is considered to be essential for the potent and selective activity seen in our previous study. The activity was maintained when the N-hydroxyformamidine moiety was replaced by an imidazole ring (3a; IC50 = 5.7 +/- 1.0 nM), but this was associated with a loss of selectivity for cytochrome P450s (CYPs). However, other azole derivatives such as isoxazole derivative 23 (IC50 value 38 +/- 10 nM) and pyrazole derivative 24 (IC50 value 23 +/- 12 nM) showed potent and selective activities with improved stability.

  DOI：

  10.1021/jm020557k

文献信息

• US4160841A
  申请人：——

  公开号：US4160841A

  公开（公告）日：1979-07-10
• US4229460A
  申请人：——

  公开号：US4229460A

  公开（公告）日：1980-10-21
• US4229581A
  申请人：——

  公开号：US4229581A

  公开（公告）日：1980-10-21
• US4232034A
  申请人：——

  公开号：US4232034A

  公开（公告）日：1980-11-04
• US4244964A
  申请人：——

  公开号：US4244964A

  公开（公告）日：1981-01-13