1-(2-fluoroethyl)-6-fluoro-7-(3-methyl-3-amino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

• 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-(2-fluoroethyl)-6-fluoro-7-(3-methyl-3-amino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 7-(3-Amino-3-methylazetidin-1-yl)-6-fluoro-1-(2-fluoroethyl)-4-oxoquinoline-3-carboxylic acid
• 化学式: C₁₆H₁₇F₂N₃O₃
• 分子量: 337.326
• InChiKey: UUXXDPWABMNWFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  24
• 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：
  86.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  6,7-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid 在 吡啶 、 sodium hydroxide 、 三乙胺 作用下， 反应 5.0h， 生成 1-(2-fluoroethyl)-6-fluoro-7-(3-methyl-3-amino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic 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

• Derivatives of 7-(1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic
  申请人：Laboratorios del Dr. Esteve S.A.

  公开号：US04927926A1

  公开（公告）日：1990-05-22

  The present invention relates to new heterocyclic compounds, derivatives of 7-(1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids, characterized in that they correspond to formula (I) ##STR1## The invention also relates to the preparation of these compounds and their applications as medicines.

  本发明涉及新的杂环化合物，即7-(1-氮杂环丙基)-1,4-二氢-4-氧代-3-喹啉羧酸衍生物，其特征在于它们符合以下式（I）##STR1## 本发明还涉及这些化合物的制备以及它们作为药物的应用。
• Dérivés des acides 7-(1-azétidinyl)-1,4-dihydro-4-oxoquinoléine-3-carboxyliques, leur préparation et leur application en tant que médicaments
  申请人：LABORATORIOS DEL DR. ESTEVE, S.A.

  公开号：EP0324298B1

  公开（公告）日：1992-12-23
• US4927926A
  申请人：——

  公开号：US4927926A

  公开（公告）日：1990-05-22
• 7-Azetidinylquinolones as antibacterial agents. Synthesis and structure-activity relationships
  作者：Jordi Frigola、Juan Pares、Jordi Corbera、David Vano、Ramon Merce、Antoni Torrens、Josep Mas、Eduard Valenti

  DOI：10.1021/jm00059a002

  日期：1993.4

  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.