1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester | 1132922-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester
• CAS: 1132922-49-6
• 化学式: C₂₁H₂₀ClNO₂
• 分子量: 353.848
• InChiKey: DWZKVGCVUGNWPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester 在 lithium hydroxide monohydrate 、 水 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以90%的产率得到1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid
  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
• 作为产物：
  描述：

  2-甲基-5-苯基-1H-吡咯-3-羧酸乙酯 、 4-氯氯苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.5h， 以48%的产率得到1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester
  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