4-oxo-1-pentyl-1,4-dihydroquinoline-3-carbaldehyde | 957066-97-6

• 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: 4-oxo-1-pentyl-1,4-dihydroquinoline-3-carbaldehyde
• 英文别名: 4-Oxo-1-pentylquinoline-3-carbaldehyde
• CAS: 957066-97-6
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: ZQFYNABOJYVZEY-UHFFFAOYSA-N

物化性质

• 沸点：
  369.4±42.0 °C(predicted)
• 密度：
  1.165±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 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：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-oxo-1-pentyl-1,4-dihydroquinoline-3-carbaldehyde 、 金刚烷胺 在 3 A molecular sieve 、 三乙胺 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以35%的产率得到3-((1-adamantyl)aminomethyl)-1-pentyl-1H-quinolin-4-one
  参考文献：
  名称：

  Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands:  Consequences in Receptor Affinity and Functionality

  摘要：

  CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo- 1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure - functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.

  DOI：

  10.1021/jm070387h
• 作为产物：
  描述：

  4-氧代-1-戊基喹啉-3-羧酸 在 四(三苯基膦)钯 氯化亚砜 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 以65%的产率得到4-oxo-1-pentyl-1,4-dihydroquinoline-3-carbaldehyde
  参考文献：
  名称：

  Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands:  Consequences in Receptor Affinity and Functionality

  摘要：

  CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo- 1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure - functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.

  DOI：

  10.1021/jm070387h

文献信息

• Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands:  Consequences in Receptor Affinity and Functionality
  作者：Eric Stern、Giulio G. Muccioli、Barbara Bosier、Laurie Hamtiaux、Régis Millet、Jacques H. Poupaert、Jean-Pierre Hénichart、Patrick Depreux、Jean-François Goossens、Didier M. Lambert

  DOI：10.1021/jm070387h

  日期：2007.11.1

  CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo- 1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure - functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.