1-cyclopropyl-5,6,8-trifluoro-1,4-dihydro-7-methoxy-4-oxo-3-quinolinecarboxylic acid | 107564-13-6

• 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-cyclopropyl-5,6,8-trifluoro-1,4-dihydro-7-methoxy-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 1-cyclopropyl-5,6,8-trifluoro-7-methoxy-4-oxoquinoline-3-carboxylic acid
• CAS: 107564-13-6
• 化学式: C₁₄H₁₀F₃NO₄
• 分子量: 313.233
• InChiKey: XHTHZDZSISDZRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  489.3±45.0 °C(Predicted)
• 密度：
  1.640±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.53
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-(pentafluorophenyl)-4,4-dimethyl-2-oxazoline 在 正丁基锂 作用下， 反应 2.33h， 生成 1-cyclopropyl-5,6,8-trifluoro-1,4-dihydro-7-methoxy-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship

  摘要：

  A series of 5-amino- and 5-hydroxyquinolone antibacterials substituted at C7 with a select group of common piperazinyl and 3-aminopyrrolidinyl side chains was prepared. These 5-substituted derivatives were compared to the analogous 5-hydrogen compounds for antiinfective activity by using DNA gyrase inhibition, minimum inhibitory concentrations against a variety of bacteria, and in vivo efficacy in the mouse infection model. The influence on the structure-activity relationships of varied substituents at C8 (H, F, Cl) and Ni (ethyl, cyclopropyl, difluorophenyl) was also studied. The results showed that several of the structure-activity conclusions regarding side-chain bulk at C7, the effect of halogen at C8, and the effect of the C5-amino group were greatly influenced by the choice of the N1-substituent. Several outstanding broad spectrum quinolones were identified in this work. In particular, the spectrum and potency of the 7-piperazinyl quinolones could be greatly enhanced by the judicious choice of C5-, C8-, and N1-substitutents.

  DOI：

  10.1021/jm00107a039