5-methoxy-4-methyl-3-phenylquinolin-2-one | 1432065-30-9

• 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: 5-methoxy-4-methyl-3-phenylquinolin-2-one
• 英文别名: 5-methoxy-4-methyl-3-phenyl-1H-quinolin-2-one
• CAS: 1432065-30-9
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: NZMXYURZRHQYIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methoxy-4-methyl-3-phenylquinolin-2-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以50%的产率得到5-hydroxy-4-methyl-3-phenylquinolin-2-one
  参考文献：
  名称：

  3-Aryl-4-methyl-2-quinolones Targeting MultiresistantStaphylococcus aureusBacteria

  摘要：

  AbstractThe NorA efflux pump lowers intracellular fluoroquinolone concentrations by expelling antibiotics through the membrane of Staphylococcus aureus. We identified 3‐aryl‐4‐methyl‐2‐quinolin‐2‐ones as compounds able to restore the activity of the NorA substrate, ciprofloxacin, against resistant S. aureus strains, and acting as efflux pump inhibitors (EPI). In particular, 5‐hydroxy‐7‐methoxy‐4‐methyl‐3‐phenylquinolin‐2‐one (6 c) presents both an EPI and an antimicrobial effect. Its efficacy and safety make it a potential candidate for further investigations.

  DOI：

  10.1002/cmdc.201200551
• 作为产物：
  描述：

  N-(2-acetyl-3-methoxyphenyl)-2-phenylacetamide 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 以65%的产率得到5-methoxy-4-methyl-3-phenylquinolin-2-one
  参考文献：
  名称：

  3-Aryl-4-methyl-2-quinolones Targeting MultiresistantStaphylococcus aureusBacteria

  摘要：

  AbstractThe NorA efflux pump lowers intracellular fluoroquinolone concentrations by expelling antibiotics through the membrane of Staphylococcus aureus. We identified 3‐aryl‐4‐methyl‐2‐quinolin‐2‐ones as compounds able to restore the activity of the NorA substrate, ciprofloxacin, against resistant S. aureus strains, and acting as efflux pump inhibitors (EPI). In particular, 5‐hydroxy‐7‐methoxy‐4‐methyl‐3‐phenylquinolin‐2‐one (6 c) presents both an EPI and an antimicrobial effect. Its efficacy and safety make it a potential candidate for further investigations.

  DOI：

  10.1002/cmdc.201200551

文献信息

• 3-Aryl-4-methyl-2-quinolones Targeting Multiresistant<i>Staphylococcus aureus</i>Bacteria
  作者：Anne Doléans-Jordheim、Jean-Baptiste Veron、Olivier Fendrich、Emmanuelle Bergeron、Adrien Montagut-Romans、Yung-Sing Wong、Bianca Furdui、Jean Freney、Charles Dumontet、Ahcène Boumendjel

  DOI：10.1002/cmdc.201200551

  日期：2013.4

  AbstractThe NorA efflux pump lowers intracellular fluoroquinolone concentrations by expelling antibiotics through the membrane of Staphylococcus aureus. We identified 3‐aryl‐4‐methyl‐2‐quinolin‐2‐ones as compounds able to restore the activity of the NorA substrate, ciprofloxacin, against resistant S. aureus strains, and acting as efflux pump inhibitors (EPI). In particular, 5‐hydroxy‐7‐methoxy‐4‐methyl‐3‐phenylquinolin‐2‐one (6 c) presents both an EPI and an antimicrobial effect. Its efficacy and safety make it a potential candidate for further investigations.