1-cyclopropyl-6-fluoro-7-{4-[(4-fluoro-benzylamino)-methyl]-[1,2,3]triazol-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester | 1416988-56-1

• 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: 1-cyclopropyl-6-fluoro-7-{4-[(4-fluoro-benzylamino)-methyl]-[1,2,3]triazol-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
• CAS: 1416988-56-1
• 化学式: C₂₅H₂₃F₂N₅O₃
• 分子量: 479.486
• InChiKey: VOKPYPSTHLUVHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  91.04
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-6-fluoro-7-{4-[(4-fluoro-benzylamino)-methyl]-[1,2,3]triazol-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 在 盐酸 作用下， 以 水 为溶剂， 反应 12.0h， 以82%的产率得到1-cyclopropyl-6-fluoro-7-{4-[(4-fluoro-benzylamino)-methyl]-[1,2,3]triazol-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of new N-substituted amino methyl-[1,2,3] triazolyl moieties of fluoroquinolones as antibacterial agents

  摘要：

  A series of twenty new N-substituted amino methyl-[1,2,3] triazolyl derivatives at C-7 position of fluoroquinolones were designed and synthesized through multistep synthesis. The synthesized compounds were characterized by H-1 NMR, C-13 NMR, ESI-MS, and IR. The antibacterial activities of these new fluoroquinolones were evaluated using a standard broth micro dilution technique. Out of the twenty derivatives, aryl substituted amino derivatives (6m to 6q) exhibited very good potency in inhibiting the growth of Methicillin-sensitive Staphylococcus aureus (MSSA), Methicillin-resistant Staphylococcus aureus (MRSA), and Vancomycin-Resistant Enterococcus faecalis (VRE faecalis) (MIC: 0.25-4.00 mu g/mL) as compared to the marketed drugs Linezolid and Ciprofloxacin.

  DOI：

  10.1007/s00044-012-0394-2
• 作为产物：
  描述：

  1-cyclopropyl-6-fluoro-7-(4-hydroxymethyl-[1,2,3]triazol-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 在 吡啶 、 氯化亚砜 、 三乙胺 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 1-cyclopropyl-6-fluoro-7-{4-[(4-fluoro-benzylamino)-methyl]-[1,2,3]triazol-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Design and synthesis of new N-substituted amino methyl-[1,2,3] triazolyl moieties of fluoroquinolones as antibacterial agents

  摘要：

  A series of twenty new N-substituted amino methyl-[1,2,3] triazolyl derivatives at C-7 position of fluoroquinolones were designed and synthesized through multistep synthesis. The synthesized compounds were characterized by H-1 NMR, C-13 NMR, ESI-MS, and IR. The antibacterial activities of these new fluoroquinolones were evaluated using a standard broth micro dilution technique. Out of the twenty derivatives, aryl substituted amino derivatives (6m to 6q) exhibited very good potency in inhibiting the growth of Methicillin-sensitive Staphylococcus aureus (MSSA), Methicillin-resistant Staphylococcus aureus (MRSA), and Vancomycin-Resistant Enterococcus faecalis (VRE faecalis) (MIC: 0.25-4.00 mu g/mL) as compared to the marketed drugs Linezolid and Ciprofloxacin.

  DOI：

  10.1007/s00044-012-0394-2