1-cyclopropyl-5-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid | 138668-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-cyclopropyl-5-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-5-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic acid
• CAS: 138668-42-5
• 化学式: C₁₈H₂₁FN₄O₃
• 分子量: 360.388
• InChiKey: FSFABDPINDVJIX-UHFFFAOYSA-N

物化性质

• 沸点：
  641.7±55.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,6-二氯-5-氟烟酸 在 sodium hydroxide 、 五氯化磷 、 乙酸酐 、 potassium carbonate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium diisopropyl amide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 27.63h， 生成 1-cyclopropyl-5-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted 6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids

  摘要：

  A series of 5-substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids have been prepared and tested for their in vitro and in vivo antibacterial activities. The 5-methyl group gave better in vitro activity with the 1-cyclopropyl appendage, but poorer activity with the 1-tert-butyl moiety. With the 1-(2,4-difluorophenyl) substitution, the influence of the 7-cycloalkylamino group was determinant: a (3S)-3-amino-pyrrolidine was shown to enhance greatly the in vitro and in vivo activity of the 5-methyl derivative. Compound 33 (BMY 43748) was selected as a promising candidate for an improved therapeutic agent.

  DOI：

  10.1021/jm00081a013

文献信息

• Antibacterial agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0326891A2

  公开（公告）日：1989-08-09

  Novel naphthyridine-, and quinolinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

  介绍了作为抗菌剂的新型萘啶酸和喹啉羧酸及其制造、配制和用于治疗细菌感染的方法，包括用于制造抗菌剂的某些新型中间体。
• ANTIBACTERIAL AGENTS
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0398967A1

  公开（公告）日：1990-11-28
• US4920120A
  申请人：——

  公开号：US4920120A

  公开（公告）日：1990-04-24
• US5585491A
  申请人：——

  公开号：US5585491A

  公开（公告）日：1996-12-17
• WO1989006649A2
  申请人：——

  公开号：WO1989006649A2

  公开（公告）日：1989-07-27