diethyl 2-((4-bromo 2-methoxyphenylamino)methylene)malonate | 1314230-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl 2-((4-bromo 2-methoxyphenylamino)methylene)malonate
• CAS: 1314230-93-7
• 化学式: C₁₅H₁₈BrNO₅
• 分子量: 372.216
• InChiKey: JAGJUDYSFCJILL-UHFFFAOYSA-N

物化性质

• 沸点：
  402.1±45.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diethyl 2-((4-bromo 2-methoxyphenylamino)methylene)malonate 在 potassium carbonate 、 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 、 sodium hydroxide 作用下， 以 二苯醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 N-(adamantan-1-yl)-6-bromo-8-methoxy-4-oxo-1-pentyl-1,4-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：

  邻甲氧基苯胺 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 2.25h， 生成 diethyl 2-((4-bromo 2-methoxyphenylamino)methylene)malonate
  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