5-amino-1-cyclopropyl-6,8-difluoro-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: 5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-3-amino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 5-Amino-7-(3-amino-3-methylazetidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid
• 化学式: C₁₇H₁₈F₂N₄O₃
• 分子量: 364.352
• InChiKey: WXMYDHQMJVPNTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-氨基-1-环丙基-6,7,8-三氟-4-氧代-1,4-二氢-3-喹啉羧酸 、 3-amino-3-methylazetidine dihydrochloride 在 吡啶 、 三乙胺 作用下， 反应 3.0h， 以92%的产率得到5-amino-1-cyclopropyl-6,8-difluoro-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

• US5393758A
  申请人：——

  公开号：US5393758A

  公开（公告）日：1995-02-28
• 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.