4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester | 1297310-86-1

• 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: 4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester
• CAS: 1297310-86-1
• 化学式: C₂₇H₂₄FNO₇
• 分子量: 493.488
• InChiKey: UZAWZOCRVIWROE-ZYNYLDFASA-N

物化性质

• 熔点：
  146 °C
• 沸点：
  669.4±55.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  111.9
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester 在 甲醇 、 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 以70%的产率得到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 sodium ethanolate 、 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 68.5h， 生成 4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester
  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