ethyl α(E)-[(diethylamino)methylene]-3-ethyl-2,4,5-trifluoro-β-oxo-benzenepropanoate | 925457-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl α(E)-[(diethylamino)methylene]-3-ethyl-2,4,5-trifluoro-β-oxo-benzenepropanoate
• 英文别名: ethyl (E)-3-(diethylamino)-2-(3-ethyl-2,4,5-trifluorobenzoyl)prop-2-enoate
• CAS: 925457-03-0
• 化学式: C₁₈H₂₂F₃NO₃
• 分子量: 357.373
• InChiKey: VAUKPESDAMLFKV-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl α(E)-[(diethylamino)methylene]-3-ethyl-2,4,5-trifluoro-β-oxo-benzenepropanoate 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 (1-cyclopropyl-8-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylato-O₃,O₄)difluoro-boron
  参考文献：
  名称：

  Design, synthesis and activity against Toxoplasma gondii, Plasmodium spp., and Mycobacterium tuberculosis of new 6-fluoroquinolones

  摘要：

  This paper reports on the rational design of a series of new 6-fluoroquinolones by QSAR analysis against Toxoplasma (T.) gondii, their synthesis, their biological evaluation against T. gondii and Plasmodium (P.) spp., and their effect on Mycobacterium (M.) tuberculosis DNA gyrase and growth inhibition. Of the 12 computer-designed 8-ethyl(or methoxy)- and 5-ethyl-8-methoxy-6-fluoroquinolones predicted to be active against T. gondii, we succeeded in the synthesis of four 6-fluoro-8-methoxy-quinolones. The four 6-fluoro-8-methoxy-quinolones are active on T. gondii but only one is as active as predicted. One of these four compounds appears to be an antiparasitical drug of great potential with inhibitory activities comparable to or higher than that of trovafloxacin, gatifloxacin, and moxifloxacin. They also inhibit DNA supercoiling by M. tuberculosis gyrase with an efficiency comparable to that of the most active quinolones but are poor inhibitors of M. tuberculosis growth. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.07.003
• 作为产物：
  描述：

  3-ethyl-2,4,5-trifluorobenzoic acid 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲苯 为溶剂， 反应 29.0h， 生成 ethyl α(E)-[(diethylamino)methylene]-3-ethyl-2,4,5-trifluoro-β-oxo-benzenepropanoate
  参考文献：
  名称：

  Design, synthesis and activity against Toxoplasma gondii, Plasmodium spp., and Mycobacterium tuberculosis of new 6-fluoroquinolones

  摘要：

  This paper reports on the rational design of a series of new 6-fluoroquinolones by QSAR analysis against Toxoplasma (T.) gondii, their synthesis, their biological evaluation against T. gondii and Plasmodium (P.) spp., and their effect on Mycobacterium (M.) tuberculosis DNA gyrase and growth inhibition. Of the 12 computer-designed 8-ethyl(or methoxy)- and 5-ethyl-8-methoxy-6-fluoroquinolones predicted to be active against T. gondii, we succeeded in the synthesis of four 6-fluoro-8-methoxy-quinolones. The four 6-fluoro-8-methoxy-quinolones are active on T. gondii but only one is as active as predicted. One of these four compounds appears to be an antiparasitical drug of great potential with inhibitory activities comparable to or higher than that of trovafloxacin, gatifloxacin, and moxifloxacin. They also inhibit DNA supercoiling by M. tuberculosis gyrase with an efficiency comparable to that of the most active quinolones but are poor inhibitors of M. tuberculosis growth. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.07.003