7-(3-氨基-1-哌啶基)-1-环丙基-6-氟-1,4-二氢-4-氧代-3-喹啉羧酸 | 138060-06-7

• 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
• 中文名称: 7-(3-氨基-1-哌啶基)-1-环丙基-6-氟-1,4-二氢-4-氧代-3-喹啉羧酸
• 英文名称: 7-(3-amino-1-piperidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 7-(3-Aminopiperidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 138060-06-7
• 化学式: C₁₈H₂₀FN₃O₃
• 分子量: 345.374
• InChiKey: PYOHRNZMZWKZPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  578.9±50.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-环丙基-6,7-二氟-1,4-二氢-4-氧喹啉-3-羧酸 、 3-氨基哌啶盐酸盐 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以65%的产率得到7-(3-氨基-1-哌啶基)-1-环丙基-6-氟-1,4-二氢-4-氧代-3-喹啉羧酸
  参考文献：
  名称：

  New 8-(trifluoromethyl)-substituted quinolones. The benefits of the 8-fluoro group with reduced phototoxic risk

  摘要：

  A series of 8-(trifluoromethyl)-substituted quinolones has been prepared and evaluated for in vitro and in vivo antibacterial activity, and phototolerance in a mouse phototolerance assay. These analogues were compared to the corresponding series of 6,8-difluoro- and 6-fluoro-8H-quinolones (ciprofloxacin type). Although their in vitro antibacterial activities are less than the 6,8-difluoro analogues, the 8-(trifluoromethyl)quinolones are generally equivalent to their 8H analogues. In vivo, they are comparable to the 6,8-difluoro series and show up to 10-fold improvement in efficacy when compared to their ciprofloxacin counterparts vs Streptococcus pyogenes and Streptococcus pneumonia. In the phototolerance model, the 8-(trifluoromethyl)quinolones are comparable to the 8H-quinolones. Both of these series display much higher no effect doses (greater tolerance) than the corresponding 6,8-difluoroquinolones.

  DOI：

  10.1021/jm00080a023

文献信息

• New 8-(trifluoromethyl)-substituted quinolones. The benefits of the 8-fluoro group with reduced phototoxic risk
  作者：J. P. Sanchez、A. J. Bridges、R. Bucsh、J. M. Domagala、R. D. Gogliotti、S. E. Hagen、C. L. Heifetz、E. T. Joannides、J. C. Sesnie

  DOI：10.1021/jm00080a023

  日期：1992.1

  A series of 8-(trifluoromethyl)-substituted quinolones has been prepared and evaluated for in vitro and in vivo antibacterial activity, and phototolerance in a mouse phototolerance assay. These analogues were compared to the corresponding series of 6,8-difluoro- and 6-fluoro-8H-quinolones (ciprofloxacin type). Although their in vitro antibacterial activities are less than the 6,8-difluoro analogues, the 8-(trifluoromethyl)quinolones are generally equivalent to their 8H analogues. In vivo, they are comparable to the 6,8-difluoro series and show up to 10-fold improvement in efficacy when compared to their ciprofloxacin counterparts vs Streptococcus pyogenes and Streptococcus pneumonia. In the phototolerance model, the 8-(trifluoromethyl)quinolones are comparable to the 8H-quinolones. Both of these series display much higher no effect doses (greater tolerance) than the corresponding 6,8-difluoroquinolones.