N-((3s,5s,7s)-adamantan-1-yl)-2-oxo-1,2-dihydroquinoline-3-carboxamide | 1314230-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-((3s,5s,7s)-adamantan-1-yl)-2-oxo-1,2-dihydroquinoline-3-carboxamide
• 英文别名: N-(adamantan-1-yl)-2-oxo-1,2-dihydroquinoline-3-carboxamide；N-(1-adamantyl)-2-oxo-1H-quinoline-3-carboxamide
• CAS: 1314230-92-6
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: OKHDVYJGORRGBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-碘戊烷 、 N-((3s,5s,7s)-adamantan-1-yl)-2-oxo-1,2-dihydroquinoline-3-carboxamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以53%的产率得到N-(adamantan-1-yl)-2-oxo-1-pentyl-1,2-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 4. Identification of New Potent and Selective Ligands for the Cannabinoid Type 2 Receptor with Diverse Substitution Patterns and Antihyperalgesic Effects in Mice

  摘要：

  Experimental evidence suggests that selective CB2 receptor modulators may provide access to antihyperalgesic agents devoid of psychotropic effects. Talcing advantage of previous findings on structure-activity/selectivity relationships for a class of 4-quinolone-3-carboxamides, further structural modifications of the heterocyclic scaffold were explored, leading to the discovery of the 8-methoxy derivative 4a endowed with the highest affinity and selectivity ever reported for a CB2 ligand. The compound, evaluated in vivo in the formalin test, behaved as an inverse agonist by reducing at a dose of 6 mg/kg the second phase of the formalin-induced nocifensive response in mice.

  DOI：

  10.1021/jm200476p
• 作为产物：
  描述：

  金刚烷胺 、 2-羟基-3-喹啉羧酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以40%的产率得到N-((3s,5s,7s)-adamantan-1-yl)-2-oxo-1,2-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 4. Identification of New Potent and Selective Ligands for the Cannabinoid Type 2 Receptor with Diverse Substitution Patterns and Antihyperalgesic Effects in Mice

  摘要：

  Experimental evidence suggests that selective CB2 receptor modulators may provide access to antihyperalgesic agents devoid of psychotropic effects. Talcing advantage of previous findings on structure-activity/selectivity relationships for a class of 4-quinolone-3-carboxamides, further structural modifications of the heterocyclic scaffold were explored, leading to the discovery of the 8-methoxy derivative 4a endowed with the highest affinity and selectivity ever reported for a CB2 ligand. The compound, evaluated in vivo in the formalin test, behaved as an inverse agonist by reducing at a dose of 6 mg/kg the second phase of the formalin-induced nocifensive response in mice.

  DOI：

  10.1021/jm200476p

文献信息

• Step-economical synthesis of 3-amido-2-quinolones by dendritic copper powder-mediated one-pot reaction
  作者：Byung Hoon Ahn、Ill Young Lee、Hee Nam Lim

  DOI：10.1039/c8ob01994k

  日期：——

  The one-pot protocol by the dendritic copper powder-mediated Knoevenagel condensation/annelation is delineated here for the synthesis of 3-amido-2-quinolones. It is practical with moisture tolerance and easy setup, and is compatible with many functional groups under mild conditions. This method was applied for the preparation of the key intermediates of biologically relevant 3-amido-2-quinolones.

  这里描述了通过树枝状铜粉介导的Knoevenagel缩合/退火的一锅法方案，用于合成3-酰胺基-2-喹诺酮。它具有耐湿性和易于设置的实用性，并且在温和条件下与许多官能团兼容。该方法用于制备生物学上相关的3-酰胺基-2-喹诺酮的关键中间体。
• Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 4. Identification of New Potent and Selective Ligands for the Cannabinoid Type 2 Receptor with Diverse Substitution Patterns and Antihyperalgesic Effects in Mice
  作者：Serena Pasquini、Maria De Rosa、Valentina Pedani、Claudia Mugnaini、Francesca Guida、Livio Luongo、Maria De Chiaro、Sabatino Maione、Stefania Dragoni、Maria Frosini、Alessia Ligresti、Vincenzo Di Marzo、Federico Corelli

  DOI：10.1021/jm200476p

  日期：2011.8.11

  Experimental evidence suggests that selective CB2 receptor modulators may provide access to antihyperalgesic agents devoid of psychotropic effects. Talcing advantage of previous findings on structure-activity/selectivity relationships for a class of 4-quinolone-3-carboxamides, further structural modifications of the heterocyclic scaffold were explored, leading to the discovery of the 8-methoxy derivative 4a endowed with the highest affinity and selectivity ever reported for a CB2 ligand. The compound, evaluated in vivo in the formalin test, behaved as an inverse agonist by reducing at a dose of 6 mg/kg the second phase of the formalin-induced nocifensive response in mice.