4-bromo-1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid adamantan-2-ylamide | 1132922-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-bromo-1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid adamantan-2-ylamide
• 英文别名: N-(2-adamantyl)-4-bromo-1-[(4-chlorophenyl)methyl]-2-methyl-5-phenylpyrrole-3-carboxamide
• CAS: 1132922-51-0
• 化学式: C₂₉H₃₀BrClN₂O
• 分子量: 537.927
• InChiKey: ARAMNTUIECTTLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid adamantan-2-ylamide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 2.0h， 以45%的产率得到4-bromo-1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid adamantan-2-ylamide
  参考文献：
  名称：

  Synthesis and characterization of a peripherally restricted CB1 cannabinoid antagonist, URB447, that reduces feeding and body-weight gain in mice

  摘要：

  Cannabinoid CB1 receptor antagonists reduce body weight in rodents and humans, but their clinical utility as anti-obesity agents is limited by centrally mediated side effects. Here, we describe the first mixed CB1 antagonist/CB2 agonist, URB447 ([4-amino-1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrol-3-yl]( phenyl) methanone), which lowers food intake and body-weight gain in mice without entering the brain or antagonizing central CB1-dependent responses. URB447 may provide a useful pharmacological tool for investigating the cannabinoid system, and might serve as a starting point for developing clinically viable CB1 antagonists devoid of central side effects. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.059

文献信息

• Synthesis and characterization of a peripherally restricted CB1 cannabinoid antagonist, URB447, that reduces feeding and body-weight gain in mice
  作者：Jesse LoVerme、Andrea Duranti、Andrea Tontini、Gilberto Spadoni、Marco Mor、Silvia Rivara、Nephi Stella、Cong Xu、Giorgio Tarzia、Daniele Piomelli

  DOI：10.1016/j.bmcl.2008.12.059

  日期：2009.2

  Cannabinoid CB1 receptor antagonists reduce body weight in rodents and humans, but their clinical utility as anti-obesity agents is limited by centrally mediated side effects. Here, we describe the first mixed CB1 antagonist/CB2 agonist, URB447 ([4-amino-1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrol-3-yl]( phenyl) methanone), which lowers food intake and body-weight gain in mice without entering the brain or antagonizing central CB1-dependent responses. URB447 may provide a useful pharmacological tool for investigating the cannabinoid system, and might serve as a starting point for developing clinically viable CB1 antagonists devoid of central side effects. (c) 2009 Elsevier Ltd. All rights reserved.