1-Cyclopropyl-6-fluoro-7-[3-methyl-3-[methyl-(2,2,2-trifluoroacetyl)amino]azetidin-1-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid | 1026928-82-4

• 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-[methyl-(2,2,2-trifluoroacetyl)amino]azetidin-1-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid
• CAS: 1026928-82-4
• 化学式: C₁₉H₁₈F₄N₄O₄
• 分子量: 442.37
• InChiKey: YSVRYVLVPJIRNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 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：
  94
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-Cyclopropyl-6-fluoro-7-[3-methyl-3-[methyl-(2,2,2-trifluoroacetyl)amino]azetidin-1-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid 在 sodium hydroxide 作用下， 反应 2.0h， 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
• 作为产物：
  描述：

  1-(diphenylmethyl)-3-methyl-3-azetidine hydrochloride 在 palladium dihydroxide 吡啶 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 3.0h， 生成 1-Cyclopropyl-6-fluoro-7-[3-methyl-3-[methyl-(2,2,2-trifluoroacetyl)amino]azetidin-1-yl]-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

• 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.