1-[2-(Dimethylamino)ethyl]-4-phenylquinolin-2-one | 1426831-89-1

• 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-(Dimethylamino)ethyl]-4-phenylquinolin-2-one
• 英文别名: 1-[2-(dimethylamino)ethyl]-4-phenylquinolin-2-one
• CAS: 1426831-89-1
• 化学式: C₁₉H₂₀N₂O
• 分子量: 292.381
• InChiKey: NMSFCMGAVJTZIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-二甲基-N'-苯基乙二胺 在 氯化亚砜 、 三氟甲磺酸 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 1-[2-(Dimethylamino)ethyl]-4-phenylquinolin-2-one
  参考文献：
  名称：

  Discovery of a novel series of quinolone α7 nicotinic acetylcholine receptor agonists

  摘要：

  High throughput screening led to the identification of a novel series of quinolone alpha 7 nicotinic acetylcholine receptor (nAChR) agonists. Optimization of an HTS hit (1) led to 4-phenyl-1-(quinuclidin-3-ylmethyl)quinolin-2(1H)-one, which was found to be potent and selective. Poor brain penetrance in this series was attributed to transporter-mediated efflux, which was in turn due to high pK(a). A novel 4-fluoroquinuclidine significantly lowered the pK(a) of the quinuclidine moiety, reducing efflux as measured by a Caco-2 assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.070