1-(tert-butyl)-7-(piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid | 116162-74-4

• 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: 1-(tert-butyl)-7-(piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: PD 135346；7-Piperazinyl-6-fluoro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid；1-(1,1-dimethylethyl)-1,4-dihydro-6-fluoro-7-piperazinyl-4-oxo-3-quinolinecarboxylic acid；3-Quinolinecarboxylic acid, 1,4-dihydro-1-(1,1-dimethylethyl)-6-fluoro-4-oxo-7-(1-piperazinyl)-；1-tert-butyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
• CAS: 116162-74-4
• 化学式: C₁₈H₂₂FN₃O₃
• 分子量: 347.389
• InChiKey: CTXPWRRGJDHGNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(tert-butyl)-7-(piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 1-tert-Butyl-6-fluoro-4-oxo-7-(4-{2-[(pyridine-4-carbonyl)-hydrazono]-propyl}-piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Novel fluoroquinolones: design, synthesis, and in vivo activity in mice against Mycobacterium tuberculosis H37Rv

  摘要：

  Novel 6,8-difluoro-1-alkyl-5-amino-1,4-dihydro-4-oxo-7-{4-substituted piperazin-1-yl}-quinoline-3-carboxylic acids, with the substituents at 4th position of piperazine being -[2(pyridine-4-carbonyl) hydrazono]propyl and -2[(pyrazine-2-carbonyl) amino] ethyl, were synthesized and evaluated in vivo against Mycobacterium tuberculosis H(37)Rv in Swiss albino mice. Test compounds exhibited activity comparable to that of sparfloxacin (survival rate, reduction of splenomegaly and reduced tubercular lesions) at a dose of 200 mg/kg. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.037
• 作为产物：
  描述：

  2-(2,4-二氯-5-氟苯甲酰基)-3-乙氧基丙烯酸乙酯 在 吡啶 、 氢氧化钾 、 sodium hydride 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 22.5h， 生成 1-(tert-butyl)-7-(piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationship of new 1-substituted derivatives

  摘要：

  A series of novel 7-piperazinyl-1-substituted-6-fluoroquinolones and naphthyridines have been prepared and their antibacterial activities evaluated. These derivatives are characterized by having alkyl, alkenyl, arylalkyl, cycloalkyl, and cycloalkenyl groups at the 1-position. As a result of this study, derivatives 7 and 26, which are substituted with tert-butyl groups at N-1, were found to possess excellent in vitro and in vivo potency, particularly against Staphylococcus aureus, comparable to that of norfloxacin or ciprofloxacin. Structure-activity relationships of N-1 substituted alkyls and cycloalkyls are also discussed.

  DOI：

  10.1021/jm00123a005

文献信息

• 1-tertiary-alkyl-substituted naphthyridine carboxylic acid antibacterial
  申请人：Bristol-Myers Company

  公开号：US04954507A1

  公开（公告）日：1990-09-04

  There are disclosed new naphthyridine- and quinoline-carboxylic acids having a 1-tertiary-alkyl substituent, compositions containing them, and their use in treating bacterial infections in warm-blooded animals. Also disclosed are novel amines and intermediates used in the preparation of the naphthyridine- and quinoline-carboxylic acids.

  公开了具有1-叔烷基取代基的新型萘啶酸和喹啉羧酸，含有它们的组合物，以及它们在治疗温血动物细菌感染中的用途。还公开了用于制备这些萘啶酸和喹啉羧酸的新颖胺和中间体。
• Certain 1-tertiary-butyl-naphthyridone carboxylic acid derivatives
  申请人：Bristol-Myers Company

  公开号：US04965273A1

  公开（公告）日：1990-10-23

  There are disclosed new naphthyridine- and quinoline-carboxylic acids having a 1-tertiary-alkyl substituent, compositions containing them, and their use in treating bacterial infections in warm-blooded animals. Also disclosed are novel amines and intermediates used in the preparation of the naphthyridine- and quinoline-carboxylic acids.

  本发明公开了具有1-三级烷基取代基的新萘啶和喹啉羧酸，包含它们的组合物以及它们在治疗温血动物的细菌感染中的应用。还公开了用于制备萘啶和喹啉羧酸的新型胺和中间体。
• 1-Tert-alkyl-substituted naphthyridine and quinoline carboxylic acids as antibacterial agents
  申请人：Bristol-Myers Squibb Company

  公开号：EP0266576A2

  公开（公告）日：1988-05-11

  There are disclosed new naphthyridine-and quinoline-carboxylic acids having a 1-tertiary-alkyl substituent, compositions containing them, and their use in treating bacterial infections in warm-blooded animals. Also disclosed are novel amines and intermediates used in the preparation of the naphthyridine-and quinoline-carboxylic acids.

  本发明公开了具有 1-叔烷基取代基的新型萘啶酸和喹啉羧酸、含有它们的组合物以及它们在治疗温血动物细菌感染中的用途。此外，还公开了用于制备萘啶和喹啉羧酸的新型胺和中间体。
• 1-TERTIARY-ALKYL-SUBSTITUTED NAPHTHYRIDINE- AND QUINOLINE-CARBOXYLIC ACID ANTIBACTERIAL AGENTS
  申请人：Bristol-Myers Company

  公开号：EP0288519A1

  公开（公告）日：1988-11-02
• EP0288519A4
  申请人：——

  公开号：EP0288519A4

  公开（公告）日：1992-04-15