6-Fluoro-1-(3-fluoro-phenyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid | 98106-16-2

• 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: 6-Fluoro-1-(3-fluoro-phenyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 6-Fluoro-1-(3-fluorophenyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• CAS: 98106-16-2
• 化学式: C₂₁H₁₉F₂N₃O₃
• 分子量: 399.397
• InChiKey: XYPRKLHPKBHNCI-UHFFFAOYSA-N

物化性质

• 沸点：
  593.5±50.0 °C(Predicted)
• 密度：
  1.409±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-(2,4-二氯-5-氟苯甲酰基)-3-乙氧基丙烯酸乙酯 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 6-Fluoro-1-(3-fluoro-phenyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of novel arylfluoroquinolone antibacterial agents

  摘要：

  A series of novel arylfluoroquinolones has been prepared. These derivatives are characterized by having a fluorine atom at the 6-position, substituted amino groups at the 7-position, and substituted phenyl groups at the 1-position. Structure-activity relationship (SAR) studies indicate that the in vitro antibacterial potency is greatest when the 1-substituent is either p-fluorophenyl or p-hydroxyphenyl and the 7-substituent is either 1-piperazinyl, 4-methyl-1-piperazinyl, or 3-amino-1-pyrrolidinyl. The electronic and spatial properties of the 1-substituent, as well as the steric bulk, play important roles in the antimicrobial potency in this class of antibacterials. As a result of this study, compounds 45 and 41 were found to possess excellent in vitro potency and in vivo efficacy.

  DOI：

  10.1021/jm00149a003

文献信息

• Inhibitors of cellular efflux pumps of microbes
  申请人：WOCKHARDT LIMITED

  公开号：US20020177559A1

  公开（公告）日：2002-11-28

  Compounds are described which are efflux pump inhibitors of cellular efflux pumps of microbes. Also described are methods of preparing such compounds, methods of using such efflux pump inhibitor compounds and pharmaceutical compositions which include such compounds.

  描述了一些化合物，它们是微生物细胞外输泵的外输泵抑制剂。还描述了制备这些化合物的方法，使用这些外输泵抑制剂化合物的方法以及包括这些化合物的制药组合物。
• INHIBITORS OF CELLULAR EFFLUX PUMPS OF MICROBES
  申请人：Wockhardt Limited

  公开号：EP1305048A2

  公开（公告）日：2003-05-02
• US7098219B2
  申请人：——

  公开号：US7098219B2

  公开（公告）日：2006-08-29
• [EN] INHIBITORS OF CELLULAR EFFLUX PUMPS OF MICROBES<br/>[FR] INHIBITEURS DE POMPES D'EFFLUX CELLULAIRE DE MICROBES
  申请人：WOCKHARDT LTD

  公开号：WO2002009758A2

  公开（公告）日：2002-02-07

  Compounds are described which are efflux pump inhibitors of cellular efflux pumps of microbes. Also described are methods of preparing such compounds, methods of using such efflux pump inhibitor compounds and pharmaceutical compositions which include such compounds.