3-(4-methoxyphenyl)-4-(p-tolyl)-1H-1,2,4-triazol-5(4H)-one | 92968-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-methoxyphenyl)-4-(p-tolyl)-1H-1,2,4-triazol-5(4H)-one
• 英文别名: 5-(4-methoxy-phenyl)-4-p-tolyl-2,4-dihydro-[1,2,4]triazol-3-one；5-(4-Methoxy-phenyl)-4-p-tolyl-2,4-dihydro-[1,2,4]triazol-3-on
• CAS: 92968-59-7
• 化学式: C₁₆H₁₅N₃O₂
• 分子量: 281.314
• InChiKey: BNIQFHNKFLIUDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.17
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-4-(p-tolyl)-1H-1,2,4-triazol-5(4H)-one 、 环己基异氰酸酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以38%的产率得到N-cyclohexyl-3-(4-methoxyphenyl)-5-oxo-4-(p-tolyl)-4,5-dihydro-1H-1,2,4-triazole-1-carboxamide
  参考文献：
  名称：

  Design, synthesis, biological evaluation, and comparative docking study of 1,2,4-triazolones as CB1 receptor selective antagonists

  摘要：

  Cannabinoids are potentially useful for the treatment of several diseases. In the present work, we report the syntheses and biological evaluations of 1,2,4-triazolone derivatives designed using a combined approach of scaffold hopping and pharmacophore-oriented method. These compounds exhibited interesting antagonistic activity to the cannabinoid CBI receptor. The preliminary structure activity relationships were further discussed. In addition, docking simulations were performed on the good bioactive compound 5c and the low potent compound 5d, respectively, on the basis of homology models of the CBI and CB2 receptors, which were constructed based on human beta 2-adrenoreceptor and optimized in a membrane environment by MD simulations. Calculation of the binding modes gave us insights into the structural requirements for improving the cannabinoid receptor bioactivity and selectivity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.018
• 作为产物：
  描述：

  对甲氧基苯甲酰肼 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 生成 3-(4-methoxyphenyl)-4-(p-tolyl)-1H-1,2,4-triazol-5(4H)-one
  参考文献：
  名称：

  Design, synthesis, biological evaluation, and comparative docking study of 1,2,4-triazolones as CB1 receptor selective antagonists

  摘要：

  Cannabinoids are potentially useful for the treatment of several diseases. In the present work, we report the syntheses and biological evaluations of 1,2,4-triazolone derivatives designed using a combined approach of scaffold hopping and pharmacophore-oriented method. These compounds exhibited interesting antagonistic activity to the cannabinoid CBI receptor. The preliminary structure activity relationships were further discussed. In addition, docking simulations were performed on the good bioactive compound 5c and the low potent compound 5d, respectively, on the basis of homology models of the CBI and CB2 receptors, which were constructed based on human beta 2-adrenoreceptor and optimized in a membrane environment by MD simulations. Calculation of the binding modes gave us insights into the structural requirements for improving the cannabinoid receptor bioactivity and selectivity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.018