1-(2-cyanoethyl)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester | 908340-52-3

• 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-(2-cyanoethyl)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 1-(2-cyanoethyl)-6,7-difluoro-4-oxoquinoline-3-carboxylate
• CAS: 908340-52-3
• 化学式: C₁₅H₁₂F₂N₂O₃
• 分子量: 306.269
• InChiKey: CZVJGIZGSIUUMC-UHFFFAOYSA-N

物化性质

• 沸点：
  484.0±45.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-cyanoethyl)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 在 lithium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 22.0h， 生成 7-[(4-tert-butoxycarbonyl)piperazin-1-yl]-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Novel Antibacterial Class:  A Series of Tetracyclic Derivatives

  摘要：

  We describe the synthesis and antibacterial activity of a series of tetracyclic naphthyridones. The members of this series act primarily via inhibition of bacterial translation and belong to the class of novel ribosome inhibitors (NRIs). In this paper we explore the structure-activity relationships (SAR) of these compounds to measure their ability both to inhibit bacterial translation and also to inhibit the growth of bacterial cells in culture. The most active of these compounds inhibit Streptococcus pneumoniae translation at concentrations of < 5 mu M and have minimum inhibitory concentrations (MICs) of < 8 mu g/mL against clinically relevant strains of bacteria.

  DOI：

  10.1021/jm060010w
• 作为产物：
  描述：

  3-氨基丙腈 、 2,4,5-三氟苯甲酰乙酸乙酯 、 原甲酸三乙酯 在 乙酸酐 、 sodium hydride 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 34.0h， 以70%的产率得到1-(2-cyanoethyl)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Novel Antibacterial Class:  A Series of Tetracyclic Derivatives

  摘要：

  We describe the synthesis and antibacterial activity of a series of tetracyclic naphthyridones. The members of this series act primarily via inhibition of bacterial translation and belong to the class of novel ribosome inhibitors (NRIs). In this paper we explore the structure-activity relationships (SAR) of these compounds to measure their ability both to inhibit bacterial translation and also to inhibit the growth of bacterial cells in culture. The most active of these compounds inhibit Streptococcus pneumoniae translation at concentrations of < 5 mu M and have minimum inhibitory concentrations (MICs) of < 8 mu g/mL against clinically relevant strains of bacteria.

  DOI：

  10.1021/jm060010w