7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | 127294-60-4

• 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-(3-aminopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 127294-60-4
• 化学式: C₁₈H₁₉F₂N₃O₃
• 分子量: 363.364
• InChiKey: PFXDGXLZRNKZKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  26
• 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：
  8

反应信息

• 作为反应物：
  描述：

  7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 在 盐酸 作用下， 以 水 为溶剂， 生成 7-(3-氨基哌啶-1-基)-1-环丙基-6-氟-8-甲氧基-4-氧代喹啉-3-羧酸
  参考文献：
  名称：

  Novel quinolonecarboxylic acid derivatives

  摘要：

  本发明的新型化合物由通式(1)表示：##STR1##其中R1是氢原子或氨基，R2是氟原子或甲氧基，R3是氢原子或含有1至3个碳原子的低级烷基，n是0或1。通式(1)的化合物表现出比已知的喹诺酮类抗生素如氧氟沙星和诺氟沙星更高的抗菌活性和更少的副作用。此外，具有通式(1)的化合物减少了通常伴随6,8-二氟喹啉类抗生素的的光毒性。

  公开号：

  US05051509A1
• 作为产物：
  描述：

  1-环丙基-6,7,8-三氟-4-氧代-1,4-二氢喹啉-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， 生成 7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  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

• JPH05112554A
  申请人：——

  公开号：JPH05112554A

  公开（公告）日：1993-05-07
• US5051509A
  申请人：——

  公开号：US5051509A

  公开（公告）日：1991-09-24
• Novel quinolonecarboxylic acid derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US05051509A1

  公开（公告）日：1991-09-24

  Novel compounds of the present invention are represented by the general formula (1) ##STR1## wherein R.sub.1 is hydrogen atom or amino, R.sub.2 is fluorine atom or methoxy, R.sub.3 is hydrogen atom or a lower alkyl having 1 to 3 carbon atoms, and n is 0 or 1. The compounds of the general formula (1) exhibit higher antibacterial activity with fewer side-effects than known quinolone antibiotics such as ofloxacin and norfloxacin. Further, the compounds having the general formula (1) have reduced phototoxicity which normally accompanies 6,8-defluoroquinoline antibiotics.

  本发明的新型化合物由通式(1)表示：##STR1##其中R1是氢原子或氨基，R2是氟原子或甲氧基，R3是氢原子或含有1至3个碳原子的低级烷基，n是0或1。通式(1)的化合物表现出比已知的喹诺酮类抗生素如氧氟沙星和诺氟沙星更高的抗菌活性和更少的副作用。此外，具有通式(1)的化合物减少了通常伴随6,8-二氟喹啉类抗生素的的光毒性。
• 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.