6-氟-4-氧代-1-戊基-7-(1H-吡咯-1-基)-1,4-二氢喹啉-3-羧酸 | 1048039-24-2

• 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
• 中文名称: 6-氟-4-氧代-1-戊基-7-(1H-吡咯-1-基)-1,4-二氢喹啉-3-羧酸
• 英文名称: 6-fluoro-4-oxo-1-pentyl-7-(1H-pyrrol-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
• CAS: 1048039-24-2
• 化学式: C₁₉H₁₉FN₂O₃
• 分子量: 342.37
• InChiKey: YIWKIYHHSQOTAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.23
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-氟-4-氧代-1-戊基-7-(1H-吡咯-1-基)-1,4-二氢喹啉-3-羧酸 、 金刚烷胺 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 1.5h， 以72%的产率得到N-(adamant-1-yl)-6-fluoro-4-oxo-1-pentyl-7-(1H-pyrrol-1-yl)-1,4-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 2. Synthesis and Structure−Activity Relationship of Potent and Selective Cannabinoid-2 Receptor Agonists Endowed with Analgesic Activity in Vivo

  摘要：

  Quinolone-3-carboxamides 11 bearing at position 5, 6, 7, or 8 diverse substituents such as halides, alkyl, aryl, alkoxy, and aryloxy groups differing in their steric/electronic properties, were prepared. The new compounds were tested in vitro for CB1 and CB2 receptor affinity in comparison with the reference compounds rimonabant and SR144528. The tested compounds exhibited CB2 affinity in the ran, e from 55.9 to 0.8 nM and CB1 affinity in the range from > 10 000 to 5.3 nM, with selectivity indeces [K-i(CB1)/K-i(CB2)] varying from > 2666.6 to 1.23. On the basis of the structure-selectivity relationship developed, the presence of a substituent at C6/C8 or C7 well accounts for the high or low CB2 selectivity, respectively. Compound 11c, characterized by high CB2 affinity and selectivity, showed analgesic activity in the formalin test of acute peripheral and inflammatory pain in mice as a result of selective CB2 agonistic activity.

  DOI：

  10.1021/jm800552f
• 作为产物：
  描述：

  ethyl 6-fluoro-4-oxo-1-pentyl-7-(1H-pyrrol-1-yl)-1,4-dihydroquinoline-3-carboxylate 在 sodium hydroxide 、 水 作用下， 反应 2.0h， 以83%的产率得到6-氟-4-氧代-1-戊基-7-(1H-吡咯-1-基)-1,4-二氢喹啉-3-羧酸
  参考文献：
  名称：

  Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 2. Synthesis and Structure−Activity Relationship of Potent and Selective Cannabinoid-2 Receptor Agonists Endowed with Analgesic Activity in Vivo

  摘要：

  Quinolone-3-carboxamides 11 bearing at position 5, 6, 7, or 8 diverse substituents such as halides, alkyl, aryl, alkoxy, and aryloxy groups differing in their steric/electronic properties, were prepared. The new compounds were tested in vitro for CB1 and CB2 receptor affinity in comparison with the reference compounds rimonabant and SR144528. The tested compounds exhibited CB2 affinity in the ran, e from 55.9 to 0.8 nM and CB1 affinity in the range from > 10 000 to 5.3 nM, with selectivity indeces [K-i(CB1)/K-i(CB2)] varying from > 2666.6 to 1.23. On the basis of the structure-selectivity relationship developed, the presence of a substituent at C6/C8 or C7 well accounts for the high or low CB2 selectivity, respectively. Compound 11c, characterized by high CB2 affinity and selectivity, showed analgesic activity in the formalin test of acute peripheral and inflammatory pain in mice as a result of selective CB2 agonistic activity.

  DOI：

  10.1021/jm800552f