N-[1-(9-Cyclopropyl-6-fluoro-3,4-dioxo-2,3,4,9-tetrahydro-isothiazolo[5,4-b]quinolin-7-yl)-3-methyl-azetidin-3-yl]-2,2,2-trifluoro-N-methyl-acetamide | 133224-81-4

• 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: N-[1-(9-Cyclopropyl-6-fluoro-3,4-dioxo-2,3,4,9-tetrahydro-isothiazolo[5,4-b]quinolin-7-yl)-3-methyl-azetidin-3-yl]-2,2,2-trifluoro-N-methyl-acetamide
• 英文别名: 9-cyclopropyl-6-fluoro-7-{3-[N-(methyl)trifluoroacetamido]-3-methyl-1-azetidinyl}-2,3,4,9-tetrahydroisothiazolo[5,4-b]quinoline-3,4-dione；N-[1-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)-3-methylazetidin-3-yl]-2,2,2-trifluoro-N-methylacetamide
• CAS: 133224-81-4
• 化学式: C₂₀H₁₈F₄N₄O₃S
• 分子量: 470.448
• InChiKey: OKMFCSVYOHVLGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  98.3
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-[1-(9-Cyclopropyl-6-fluoro-3,4-dioxo-2,3,4,9-tetrahydro-isothiazolo[5,4-b]quinolin-7-yl)-3-methyl-azetidin-3-yl]-2,2,2-trifluoro-N-methyl-acetamide 在 sodium hydroxide 作用下， 反应 2.0h， 生成 9-cyclopropyl-6-fluoro-7-(3-methylamino-3-methyl-1-azetidinyl)-2,3,4,9-tetrahydroisothiazolo[5,4-b]quinoline-3,4-dione
  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 N-[1-(9-Cyclopropyl-6-fluoro-3,4-dioxo-2,3,4,9-tetrahydro-isothiazolo[5,4-b]quinolin-7-yl)-3-methyl-azetidin-3-yl]-2,2,2-trifluoro-N-methyl-acetamide
  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

• Substituted azetidinylisothiazolopyridone derivatives, their preparation
  申请人：Laboratorios del Dr. Esteve

  公开号：US05087621A1

  公开（公告）日：1992-02-11

  The present invention relates to substituted azetidinylisothiazolopyridone derivatives which correspond to the general formula I: ##STR1## or its tautomeric formula ##STR2## It also relates to a process for preparing them and to their application as a medicinal product.

  本发明涉及替代了氮杂环丙烷基异噻唑吡啶酮衍生物，其对应于一般式I：##STR1## 或其互变异构式##STR2##，还涉及制备它们的方法以及它们作为药物产品的应用。