1H-Imidazole-4-carboxylic acid, 1-(4-chlorophenyl)-2-phenyl- | 942435-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1H-Imidazole-4-carboxylic acid, 1-(4-chlorophenyl)-2-phenyl-
• 英文别名: 1-(4-chlorophenyl)-2-phenylimidazole-4-carboxylic acid
• CAS: 942435-55-4
• 化学式: C₁₆H₁₁ClN₂O₂
• 分子量: 298.729
• InChiKey: ODTKSEQOCSIKQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1H-Imidazole-4-carboxylic acid, 1-(4-chlorophenyl)-2-phenyl- 、 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-phenyl-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
• 作为产物：
  描述：

  在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 1H-Imidazole-4-carboxylic acid, 1-(4-chlorophenyl)-2-phenyl-
  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

文献信息

• Optimization of imidazole amide derivatives as cannabinoid-1 receptor antagonists for the treatment of obesity
  作者：Roger A. Smith、Zahra Fathi、Furahi Achebe、Christiana Akuche、Su-Ellen Brown、Soongyu Choi、Jianmei Fan、Susan Jenkins、Harold C.E. Kluender、Anish Konkar、Rico Lavoie、Ronald Mays、Jennifer Natoli、Stephen J. O’Connor、Astrid A. Ortiz、Ning Su、Christy Taing、Susan Tomlinson、Theresa Tritto、Gan Wang、Stephan-Nicholas Wirtz、Wai Wong、Xiao-Fan Yang、Shihong Ying、Zhonghua Zhang

  DOI：10.1016/j.bmcl.2007.03.011

  日期：2007.5

  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.