1-(2-phenylethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 23845-02-5

• 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: 1-(2-phenylethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: N-(2-Phenylethyl)-4(1H)-chinolon-3-carbonsaeure；4-Oxo-1-phenethyl-1,4-dihydro-3-quinolinecarboxylic acid；4-oxo-1-(2-phenylethyl)quinoline-3-carboxylic acid
• CAS: 23845-02-5
• 化学式: C₁₈H₁₅NO₃
• mdl: MFCD25952821
• 分子量: 293.322
• InChiKey: DKABONKAWLCSRC-UHFFFAOYSA-N

物化性质

• 熔点：
  >200 °C
• 沸点：
  472.110±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.300±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二甲基金刚胺 、 1-(2-phenylethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 在 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 以25%的产率得到N-(3,5-dimethyl-1-adamantyl)-4-oxo-1-(2-phenylethyl)quinoline-3-carboxamide
  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：

  1-(2-phenylethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 在 lithium hydroxide 作用下， 生成 1-(2-phenylethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Parallel synthesis of N-biaryl quinolone carboxylic acids as selective M1 positive allosteric modulators

  摘要：

  An iterative analog library synthesis approach was employed in the exploration of a quinolone carboxylic acid series of selective M-1 positive allosteric modulators, and strategies for improving potency and plasma free fraction were identified. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.100