1-(4-chlorophenyl)-N-cyclohexyl-2-(2-methylphenyl)-1H-imidazole-4-carboxamide | 527367-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-chlorophenyl)-N-cyclohexyl-2-(2-methylphenyl)-1H-imidazole-4-carboxamide
• 英文别名: 1-(4-chlorophenyl)-N-cyclohexyl-2-o-tolyl-1H-imidazole-4-carboxamide；1-(4-chlorophenyl)-N-cyclohexyl-2-(2-methylphenyl)imidazole-4-carboxamide
• CAS: 527367-43-7
• 化学式: C₂₃H₂₄ClN₃O
• 分子量: 393.916
• InChiKey: CBCVCXIOKPCZSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(4-Chlorophenyl)-2-(2-methylphenyl)imidazole-4-carboxylic acid 、 环己胺 在 fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 1-(4-chlorophenyl)-N-cyclohexyl-2-(2-methylphenyl)-1H-imidazole-4-carboxamide
  参考文献：
  名称：

  Optimization of imidazole amide derivatives as cannabinoid-1 receptor antagonists for the treatment of obesity

  摘要：

  Several imidazole-based cyclohexyl amides were identified as potent CB-1 antagonists, but they exhibited poor oral exposure in rodents. Incorporation of a hydroxyl moiety on the cyclohexyl ring provided a dramatic improvement in oral exposure, together with a ca. 10-fold decrease in potency. Further optimization provided the imidazole 2-hydroxy-cyclohexyl amide 45, which exhibited hCB-1 K-i = 3.7 nM and caused significant appetite suppression and robust, dose-dependent reduction of body weight gain in industry-standard rat models. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.011