ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-(trifluoromethyl)-3-quinolinecarboxylate | 118829-16-6

• 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: ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-(trifluoromethyl)-3-quinolinecarboxylate
• 英文别名: 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-(trifluoromethyl)-3-quinolinecarboxylic acid,ethyl ester；1-cyclopropyl-6,7-difluoro-8-trifluoromethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester；Ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-8-(trifluoromethyl)quinoline-3-carboxylate
• CAS: 118829-16-6
• 化学式: C₁₆H₁₂F₅NO₃
• 分子量: 361.268
• InChiKey: OUKMZWIMFISXRO-UHFFFAOYSA-N

物化性质

• 熔点：
  174-179 °C
• 沸点：
  428.3±45.0 °C(Predicted)
• 密度：
  1.517±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-(trifluoromethyl)-3-quinolinecarboxylate 在 盐酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 47.0h， 生成 1-环丙基-6-氟-4-氧代-7-哌嗪-1-基-8-(三氟甲基)喹啉-3-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
• 作为产物：
  描述：

  2,-三氟-(氟甲基)苯甲酸 在 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 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 144.33h， 生成 ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-(trifluoromethyl)-3-quinolinecarboxylate
  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

• REMEDIES OR PREVENTIVES FOR AIDS
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0878194A1

  公开（公告）日：1998-11-18

  The present invention is to provide the combined use of one kind or two or more kinds of a quinolone carboxylic acid having anti-HIV activity and one kind or two or more kinds of a reverse transcriptase inhibitor or HIV protease inhibitor, and an AIDS therapeutic agent or preventive agent containing as its active ingredients one kind or two or more kinds of a quinolone carboxylic acid having anti-HIV activity and one kind or two or more kinds of a reverse transcriptase inhibitor or HIV protease inhibitor.

  本发明提供了一种或两种或两种以上具有抗HIV活性的喹诺酮羧酸与一种或两种或两种以上的逆转录酶抑制剂或HIV蛋白酶抑制剂的联合使用，以及一种包含作为其活性成分的抗HIV活性的喹诺酮羧酸和一种或两种或两种以上的逆转录酶抑制剂或HIV蛋白酶抑制剂的艾滋病治疗剂或预防剂。
• 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.

  描述了一系列新的喹诺酮羧酸，用作抗菌剂。还描述了制备化合物的方法，使用化合物的方法以及含有它们的组合物。还描述了某些新的中间体。
• Quinolone and naphthyridine antibacterial agents containing an alpha-amino acid in the side chain of the 7-substituent
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0304087A2

  公开（公告）日：1989-02-22

  Novel quinolone and naphthyridine antibacterial agents of the formula I are herein described having improved in vivo activity both orally and subcutaneously where the 7-side chain of such compounds contain an a-amino acid; also described are its corresponding optical isomers, methods of preparation as well as pharmaceutical useful intreating infectious diseases.

  本文描述了式 I 的新型喹诺酮类和萘啶类抗菌剂，其口服和皮下注射活性均有所提高。 所述的新型喹诺酮类和萘啶类抗菌剂具有更好的口服和皮下注射活性，其中此类化合物的 7 侧链含有 a-氨基酸；还描述了其相应的光学异构体、制备方法以及治疗传染性疾病的药物用途。
• Quinolones as antibacterial agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0302525A2

  公开（公告）日：1989-02-08

  A novel series of quinolone carboxylic acid derivatives of the formula 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.

  本研究描述了一系列新型喹诺酮羧酸衍生物，其式为 描述了用作抗菌剂的一系列新型喹诺酮羧酸衍生物。还描述了制造这些化合物的方法、使用这些化合物的方法以及含有这些化合物的组合物。还介绍了某些新型中间体。
• BRIDGES, ALEXANDER J.;DOMAGALA, JOHN M.
  作者：BRIDGES, ALEXANDER J.、DOMAGALA, JOHN M.

  DOI：——

  日期：——