1-cyclopropyl-7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-4-oxo-8-(trifluoromethyl)-3-quinolinecarboxylic acid | 118829-08-6

• 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-7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-4-oxo-8-(trifluoromethyl)-3-quinolinecarboxylic acid
• 英文别名: 1-Cyclopropyl-7-[3-(ethylaminomethyl)pyrrolidin-1-yl]-6-fluoro-4-oxo-8-(trifluoromethyl)quinoline-3-carboxylic acid
• CAS: 118829-08-6
• 化学式: C₂₁H₂₃F₄N₃O₃
• 分子量: 441.426
• InChiKey: YNUWDZOIKHYORM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,-三氟-(氟甲基)苯甲酸 在 盐酸 、 草酰氯 、 异丙基氯化镁 、 乙酸酐 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 173.33h， 生成 1-cyclopropyl-7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-4-oxo-8-(trifluoromethyl)-3-quinolinecarboxylic 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

• Quinolones as antibacterial agents
  申请人：Warner-Lambert Company

  公开号：US04933335A1

  公开（公告）日：1990-06-12

  A novel series of quinolone carboxylic acids for use as antibacterial agents are described. Methods for making the compounds, methods of using the compounds and compositions containing them are also described. Certain novel intermediates are also described.

  本文描述了一系列喹诺酮羧酸类化合物，用作抗菌剂。描述了制备这些化合物的方法、使用这些化合物的方法以及含有它们的组合物。还描述了某些新颖的中间体。
• 8-trifluoromethyl quinolones as antibacterial agents
  申请人：Warner-Lambert Company

  公开号：US04780468A1

  公开（公告）日：1988-10-25

  A novel series of quinolone carboxylic acids for use as antibacterial agents are described. Methods for making the compounds, methods of using the compounds and compositions containing them are also described. Certain novel intermediates are also described.

  本文描述了一系列新型的喹诺酮羧酸，可用作抗菌剂。同时还描述了制备这些化合物的方法、使用这些化合物的方法以及含有这些化合物的组合物。还描述了某些新型中间体。
• BRIDGES, ALEXANDER J.;DOMAGALA, JOHN M.
  作者：BRIDGES, ALEXANDER J.、DOMAGALA, JOHN M.

  DOI：——

  日期：——
• US4780468A
  申请人：——

  公开号：US4780468A

  公开（公告）日：1988-10-25
• US4803205A
  申请人：——

  公开号：US4803205A

  公开（公告）日：1989-02-07