1-butyl-2-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxylic acid | 1436631-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-butyl-2-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxylic acid
• CAS: 1436631-32-1
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: FBMCQKNXNPJSPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-butyl-2-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxylic acid 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 N-benzyl-1-butyl-2-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide
  参考文献：
  名称：

  Selective CB2 agonists with anti-pruritic activity: Discovery of potent and orally available bicyclic 2-pyridones

  摘要：

  The CB2 receptor has emerged as a potential target for the treatment of pruritus as well as pain without CB1-mediated side effects. We previously identified 2-pyridone derivatives 1 and 2 as potent CB2 agonists; however, this series of compounds was found to have unacceptable pharmacokinetic profiles with no significant effect in vivo. To improve these profiles, we performed further structural optimization of 1 and 2, which led to the discovery of bicyclic 2-pyridone 18e with improved CB2 affinity and selectivity over CB1. In a mouse pruritus model, 18e inhibited compound 48/80 induced scratching behavior at a dose of 100 mg/kg. In addition, the docking model of 18e with an active-state CB2 homology model indicated the structural basis of its high affinity and selectivity over CB1. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.03.030
• 作为产物：
  描述：

  1-Butylimino-cyclopentan 在 水 、 sodium hydroxide 作用下， 以 乙醇 、 二乙二醇二甲醚 为溶剂， 反应 4.5h， 生成 1-butyl-2-oxo-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxylic acid
  参考文献：
  名称：

  Selective CB2 agonists with anti-pruritic activity: Discovery of potent and orally available bicyclic 2-pyridones

  摘要：

  The CB2 receptor has emerged as a potential target for the treatment of pruritus as well as pain without CB1-mediated side effects. We previously identified 2-pyridone derivatives 1 and 2 as potent CB2 agonists; however, this series of compounds was found to have unacceptable pharmacokinetic profiles with no significant effect in vivo. To improve these profiles, we performed further structural optimization of 1 and 2, which led to the discovery of bicyclic 2-pyridone 18e with improved CB2 affinity and selectivity over CB1. In a mouse pruritus model, 18e inhibited compound 48/80 induced scratching behavior at a dose of 100 mg/kg. In addition, the docking model of 18e with an active-state CB2 homology model indicated the structural basis of its high affinity and selectivity over CB1. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.03.030