(E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate | 1297310-96-3

• 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: (E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate
• 英文别名: ethyl (E)-3-[3-acetyl-1-[(4-fluorophenyl)methyl]-4-oxoquinolin-6-yl]prop-2-enoate
• CAS: 1297310-96-3
• 化学式: C₂₃H₂₀FNO₄
• 分子量: 393.415
• InChiKey: GHMGAFMOPILISZ-YRNVUSSQSA-N

物化性质

• 熔点：
  220 °C
• 沸点：
  587.1±50.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate 在 甲醇 、 sodium ethanolate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.5h， 生成 4-[6-((E)-3-hydroxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling studies of quinolonyl diketo acid derivatives: New structural insight into the HIV-1 integrase inhibition

  摘要：

  New quinolonyl diketo acid compounds bearing various substituents at position 6 of the quinolone scaffold were designed and synthesized as potential HIV-1 integrase inhibitors. These new compounds were evaluated for their antiviral and anti-integrase activity and showed inhibitory potency similar to that of 6-bromide analog 2. Molecular modeling and docking studies were performed to rationalize these data and to provide a detailed understanding of the mechanism of inhibition for this class of compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.028
• 作为产物：
  描述：

  3-acetyl-6-bromo-1-((4-fluorophenyl)methyl)-4(1H)-quinolinone 、 丙烯酸乙酯 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以62%的产率得到(E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling studies of quinolonyl diketo acid derivatives: New structural insight into the HIV-1 integrase inhibition

  摘要：

  New quinolonyl diketo acid compounds bearing various substituents at position 6 of the quinolone scaffold were designed and synthesized as potential HIV-1 integrase inhibitors. These new compounds were evaluated for their antiviral and anti-integrase activity and showed inhibitory potency similar to that of 6-bromide analog 2. Molecular modeling and docking studies were performed to rationalize these data and to provide a detailed understanding of the mechanism of inhibition for this class of compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.028

文献信息

• Synthesis, biological evaluation and molecular modeling studies of quinolonyl diketo acid derivatives: New structural insight into the HIV-1 integrase inhibition
  作者：Pierre Vandurm、Allan Guiguen、Christine Cauvin、Benoît Georges、Kiet Le Van、Catherine Michaux、Christelle Cardona、Gladys Mbemba、Jean-François Mouscadet、László Hevesi、Carine Van Lint、Johan Wouters

  DOI：10.1016/j.ejmech.2011.02.028

  日期：2011.5

  New quinolonyl diketo acid compounds bearing various substituents at position 6 of the quinolone scaffold were designed and synthesized as potential HIV-1 integrase inhibitors. These new compounds were evaluated for their antiviral and anti-integrase activity and showed inhibitory potency similar to that of 6-bromide analog 2. Molecular modeling and docking studies were performed to rationalize these data and to provide a detailed understanding of the mechanism of inhibition for this class of compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.