methyl 6-bromo-2-butyl-1,4-dihydro-4-oxoquinoline-3-carboxylate | 1314230-90-4

• 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: methyl 6-bromo-2-butyl-1,4-dihydro-4-oxoquinoline-3-carboxylate
• 英文别名: methyl 6-bromo-2-butyl-4-oxo-1H-quinoline-3-carboxylate
• CAS: 1314230-90-4
• 化学式: C₁₅H₁₆BrNO₃
• 分子量: 338.201
• InChiKey: ZPFCHMMRQWKPGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6-bromo-2-butyl-1,4-dihydro-4-oxoquinoline-3-carboxylate 在 水 、 sodium hydroxide 作用下， 反应 1.0h， 生成
  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：

  5-溴靛红酸酐 、 3-酮庚酸甲酯 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以47%的产率得到methyl 6-bromo-2-butyl-1,4-dihydro-4-oxoquinoline-3-carboxylate
  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

• 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.