ethyl 2-chloro-α-[(dimethylamino)methylene]-4-fluoro-3-methyl-β-oxo-benzenepropanoate | 184680-78-2

• 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 2-chloro-α-[(dimethylamino)methylene]-4-fluoro-3-methyl-β-oxo-benzenepropanoate
• 英文别名: Ethyl 2-(2-chloro-4-fluoro-3-methylbenzoyl)-3-(dimethylamino)prop-2-enoate
• CAS: 184680-78-2
• 化学式: C₁₅H₁₇ClFNO₃
• 分子量: 313.756
• InChiKey: WTQUNMBOXFBMEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-chloro-α-[(dimethylamino)methylene]-4-fluoro-3-methyl-β-oxo-benzenepropanoate 在 盐酸 、 potassium carbonate 作用下， 反应 5.25h， 生成 1-cyclopropyl-7-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Potent 6-Desfluoro-8-methylquinolones as New Lead Compounds in Antibacterial Chemotherapy

  摘要：

  In a furtherance of our SAR study on the C-6 position of quinolone antibacterials, a series of 6-desfluoro-8-methylquinolones were synthesized and evaluated for their in vitro antimicrobial activity. As a result of this study, compounds with strong activity against Gram-positive bacteria, including ciprofloxacin-resistant and methicillin-resistant Staphylococcus aureus, were identified. The best Gram-positive antibacterial activity was exhibited by piperidinyl derivative 6c, which was 17 times more potent than ciprofloxacin and displayed extremely high activity against Streptococcus pneumoniae with an MIC value of less than or equal to 0.016 mu g/mL. Thus, we have shown that substituent combinations in the quinolone ring, excluding the C-6 fluorine atom, might produce powerful antibacterial agents.

  DOI：

  10.1021/jm960414w
• 作为产物：
  描述：

  2-氯-4-氟-3-甲基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 ethyl 2-chloro-α-[(dimethylamino)methylene]-4-fluoro-3-methyl-β-oxo-benzenepropanoate
  参考文献：
  名称：

  Potent 6-Desfluoro-8-methylquinolones as New Lead Compounds in Antibacterial Chemotherapy

  摘要：

  In a furtherance of our SAR study on the C-6 position of quinolone antibacterials, a series of 6-desfluoro-8-methylquinolones were synthesized and evaluated for their in vitro antimicrobial activity. As a result of this study, compounds with strong activity against Gram-positive bacteria, including ciprofloxacin-resistant and methicillin-resistant Staphylococcus aureus, were identified. The best Gram-positive antibacterial activity was exhibited by piperidinyl derivative 6c, which was 17 times more potent than ciprofloxacin and displayed extremely high activity against Streptococcus pneumoniae with an MIC value of less than or equal to 0.016 mu g/mL. Thus, we have shown that substituent combinations in the quinolone ring, excluding the C-6 fluorine atom, might produce powerful antibacterial agents.

  DOI：

  10.1021/jm960414w