1-cyclopropyl-6-fluoro-7-(3-methyl-3-methylamino-1-azetidinyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

• 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-6-fluoro-7-(3-methyl-3-methylamino-1-azetidinyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-6-fluoro-7-[3-methyl-3-(methylamino)azetidin-1-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid
• 化学式: C₁₇H₁₉FN₄O₃
• 分子量: 346.361
• InChiKey: BMNZASBHHILOAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  环丙基萘啶羧酸 在 吡啶 、 sodium hydroxide 、 三乙胺 作用下， 反应 5.0h， 生成 1-cyclopropyl-6-fluoro-7-(3-methyl-3-methylamino-1-azetidinyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  7-Azetidinylquinolones as antibacterial agents. Synthesis and structure-activity relationships

  摘要：

  A series of novel antibacterial quinolones and naphthyridones has been prepared which contain 7-azetidinyl substituents in place of the usual piperazine or aminopyrrolidine groups. These azetidinyl derivatives were evaluated for in vitro activity by determining minimum inhibitory concentrations against a variety of bacteria. In vivo efficacy in the mouse infection model and blood levels in the mouse were determined for several compounds. The influence on the structure-activity relationships of varying substituents in the azetidine ring and at position 8 (CH, CF, CCl, N) and N-1 (ethyl, fluoroethyl, cyclopropyl, tert-butyl, 4-fluorophenyl, and 2,4-difluorophenyl) was also studied. Compounds with outstandingly broad-spectrum activity, particularly against Gram-positive organisms, improved in vivo efficacy, and high blood levels were identified in this work. 7-Azetidinyl-8-chloroquinolones were considered as warranting further development.

  DOI：

  10.1021/jm00059a002

文献信息

• Dérivés d'acides pyridone carboxyliques azétidinyl substitues, leur préparation et leur application en tant que médicaments
  申请人：LABORATORIOS DEL DR. ESTEVE, S.A.

  公开号：EP0388298B1

  公开（公告）日：1995-06-21
• EP0552284A4
  申请人：——

  公开号：EP0552284A4

  公开（公告）日：1994-03-23
• ISOLATED METALLOPOLYPEPTIDE: COMPOSITIONS AND SYNTHETIC METHODS
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：EP0552284A1

  公开（公告）日：1993-07-28
• US5393758A
  申请人：——

  公开号：US5393758A

  公开（公告）日：1995-02-28
• US5408036A
  申请人：——

  公开号：US5408036A

  公开（公告）日：1995-04-18