ethyl (2Z)-3-hydroxy-3-(4-propoxyphenyl)acrylate | 1319210-00-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (2Z)-3-hydroxy-3-(4-propoxyphenyl)acrylate
• 英文别名: ethyl (Z)-3-hydroxy-3-(4-propoxyphenyl)prop-2-enoate
• CAS: 1319210-00-8
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: GCGKPOQMQMXKHD-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2Z)-3-hydroxy-3-(4-propoxyphenyl)acrylate 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 20.0~90.0 ℃ 、500.01 kPa 条件下， 反应 79.17h， 生成 N,N-diethyl-2-{[6-(3-morpholin-4-ylpropoxy)-2-(4-propoxyphenyl)quinolin-4-yl]oxy}ethanamine
  参考文献：
  名称：

  Studies on 2-phenylquinoline Staphylococcus aureus NorA efflux pump inhibitors: New insights on the C-6 position

  摘要：

  The alarming and rapid spread of antimicrobial resistance among bacteria represents a high risk for global health. Targeting factors involved in resistance to restore the activity of failing antibiotics is a promising strategy to overcome this urgent medical need. Efflux pump inhibitors are able to increase antibiotic concentrations in bacteria, thus they can be considered true antimicrobial resistance breakers. In this work, continuing our studies on inhibitors of the Staphylococcus aureus NorA pump, we designed, synthesized and biologically evaluated novel 2-phenylquinoline derivatives starting from our hits 1 and 2. Two of the synthesized compounds (6 and 7) bearing a C-6 benzyloxy group showed the best NorA inhibition activity, thereby providing an excellent starting point to direct future chemical optimizations. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.06.013
• 作为产物：
  描述：

  1-(4-丙氧基-苯基)-乙酮 、 碳酸二乙酯 在 sodium hydride 作用下， 反应 1.0h， 以76%的产率得到ethyl (2Z)-3-hydroxy-3-(4-propoxyphenyl)acrylate
  参考文献：
  名称：

  Evolution from a Natural Flavones Nucleus to Obtain 2-(4-Propoxyphenyl)quinoline Derivatives As Potent Inhibitors of the S. aureus NorA Efflux Pump

  摘要：

  Overexpression of efflux pumps is an important mechanism by which bacteria evade the effects of substrate antimicrobial agents. Inhibition of such pumps is a promising strategy to circumvent this resistance mechanism. NorA is a Staphylococcus aureus efflux pump that confers reduced susceptibility to many structurally unrelated agents, including fluoroquinolones, resulting in a multidrug resistant phenotype. In this work, a series of 2-phenyl-4(1H)-quinolone and 2-phenyl-4-hydroxyquinoline derivatives, obtained by modifying the flavone nucleus of known efflux pump inhibitors (EPIs), were synthesized in an effort to identify more potent S. aureus NorA EPIs. The 2-phenyl-4-hydroxyquinoline derivatives 28f and 29f display potent EPI activity against SA-1199B, a strain that overexpresses norA, in an ethidium bromide efflux inhibition assay. The same compounds, in combination with ciprofloxacin, were able to completely restore its antibacterial activity against both S. aureus SA-K2378 and SA-1199B, narA-overexpressing strains.

  DOI：

  10.1021/jm200370y