7-(4-formylpiperazin-1-yl)-1-ethyl-6-fluoroquinoline-4-one | 959774-07-3

• 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: 7-(4-formylpiperazin-1-yl)-1-ethyl-6-fluoroquinoline-4-one
• 英文别名: MBX 2194；4-(1-Ethyl-6-fluoro-4-oxoquinolin-7-yl)piperazine-1-carbaldehyde
• CAS: 959774-07-3
• 化学式: C₁₆H₁₈FN₃O₂
• 分子量: 303.336
• InChiKey: BOTJVKBBUITCAH-UHFFFAOYSA-N

物化性质

• 沸点：
  548.3±50.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(4-formylpiperazin-1-yl)-1-ethyl-6-fluoroquinoline-4-one 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以73%的产率得到诺氟沙星杂质D
  参考文献：
  名称：

  Preparation and antibacterial evaluation of decarboxylated fluoroquinolones

  摘要：

  Decarboxylated ciprofloxacin (3) has been reported in the literature to have antibacterial activities against Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Bacillus subtilis, Enterobacter cloacae, Serratia marcescens and especially potent activity against Escherichia coli. Herein, we report our syntheses of 3 and five additional decarboxylated fluoroquinolones (FQs). We have re-evaluated the antibacterial activity of these FQs. In contrast to previously reported data, none of these decarboxylated fluoroquinolones showed significant antibacterial activity in our assays using both the broth dilution and agar methods. Our study confirmed that the presence of a carboxylic acid group at the 3-position of the fluoroquinolone scaffold is essential for antibacterial activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.060
• 作为产物：
  描述：

  诺氟沙星 、 N,N-二甲基甲酰胺 在 potassium cyanide 作用下， 反应 24.0h， 以95%的产率得到7-(4-formylpiperazin-1-yl)-1-ethyl-6-fluoroquinoline-4-one
  参考文献：
  名称：

  Preparation and antibacterial evaluation of decarboxylated fluoroquinolones

  摘要：

  Decarboxylated ciprofloxacin (3) has been reported in the literature to have antibacterial activities against Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Bacillus subtilis, Enterobacter cloacae, Serratia marcescens and especially potent activity against Escherichia coli. Herein, we report our syntheses of 3 and five additional decarboxylated fluoroquinolones (FQs). We have re-evaluated the antibacterial activity of these FQs. In contrast to previously reported data, none of these decarboxylated fluoroquinolones showed significant antibacterial activity in our assays using both the broth dilution and agar methods. Our study confirmed that the presence of a carboxylic acid group at the 3-position of the fluoroquinolone scaffold is essential for antibacterial activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.060

文献信息

• Preparation and antibacterial evaluation of decarboxylated fluoroquinolones
  作者：Son T. Nguyen、Xiaoyuan Ding、Michelle M. Butler、Tommy F. Tashjian、Norton P. Peet、Terry L. Bowlin

  DOI：10.1016/j.bmcl.2011.07.060

  日期：2011.10

  Decarboxylated ciprofloxacin (3) has been reported in the literature to have antibacterial activities against Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Bacillus subtilis, Enterobacter cloacae, Serratia marcescens and especially potent activity against Escherichia coli. Herein, we report our syntheses of 3 and five additional decarboxylated fluoroquinolones (FQs). We have re-evaluated the antibacterial activity of these FQs. In contrast to previously reported data, none of these decarboxylated fluoroquinolones showed significant antibacterial activity in our assays using both the broth dilution and agar methods. Our study confirmed that the presence of a carboxylic acid group at the 3-position of the fluoroquinolone scaffold is essential for antibacterial activity. (C) 2011 Elsevier Ltd. All rights reserved.