ethyl 3-oxo-3-(3,4,6-trifluoro-2-methoxyphenyl)propanoate | 124487-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-oxo-3-(3,4,6-trifluoro-2-methoxyphenyl)propanoate
• CAS: 124487-32-7
• 化学式: C₁₂H₁₁F₃O₄
• 分子量: 276.212
• InChiKey: LIPZIFQSAPANQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-oxo-3-(3,4,6-trifluoro-2-methoxyphenyl)propanoate 在 potassium tert-butylate 、 乙酸酐 作用下， 以 叔丁醇 为溶剂， 反应 12.5h， 生成 ethyl 1-cyclopropyl-6,7-difluoro-5-methoxy-4-oxoquinoline-3-carboxylate
  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
• 作为产物：
  描述：

  2,3,4,6-四氟苯甲酸 在 正丁基锂 、 dipyridyl 、 草酰氯 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 ethyl 3-oxo-3-(3,4,6-trifluoro-2-methoxyphenyl)propanoate
  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

文献信息

• HAKAHO, DZYUNDZI;OKATA, XIDEHTSUGI;XIROSEH, TORU;MATSUMOTO, DZYUNITI;NAKA+
  作者：HAKAHO, DZYUNDZI、OKATA, XIDEHTSUGI、XIROSEH, TORU、MATSUMOTO, DZYUNITI、NAKA+

  DOI：——

  日期：——