4-(2-propyn-1-yloxy)-7-(trifluoromethyl)quinoline | 1141428-34-3

• 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: 4-(2-propyn-1-yloxy)-7-(trifluoromethyl)quinoline
• CAS: 1141428-34-3
• 化学式: C₁₃H₈F₃NO
• 分子量: 251.208
• InChiKey: QTOYROFJRVGTCK-UHFFFAOYSA-N

物化性质

• 沸点：
  308.0±42.0 °C(predicted)
• 密度：
  1.314±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  22.12
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(2-propyn-1-yloxy)-7-(trifluoromethyl)quinoline 、 氯代肟基乙酸乙酯 在 三乙胺 作用下， 以 乙醚 为溶剂， 以56%的产率得到5-[[[7-(trifluoromethyl)-4-quinolinyl]oxy]methyl]-3-isoxazolecarboxylic acid ethyl ester
  参考文献：
  名称：

  Structure−Activity Relationships for a Series of Quinoline-Based Compounds Active against Replicating and Nonreplicating Mycobacterium tuberculosis

  摘要：

  Tuberculosis (TB) remains as a global pandemic that is aggravated by a lack of health care, the spread of HIV, and the emergence of multidrug-resistant TB (MDR-TB) and extensively drug-resistant TB (XDR-TB) strains. New anti-TB drugs are urgently required to shorten the long 6-12 month treatment regimen and to battle drug-resistant Mtb strains. We have identified several potent quinoline-based anti-TB compounds, bearing an isoxazole containing side-chain. The most potent compounds, 7g and 13, exhibited submicromolar activity against the replicating bacteria (R-TB), with minimum inhibitory concentrations (MICs) of 0.77 and 0.95 mu M, respectively. In general, these compounds also had micromolar activity against the nonreplicating persistent bacteria (NRP-TB) and did not show toxicity on Vero cells up to 128 mu M concentration. Compounds 7g and 13 were shown to retain their anti-TB activity against rifampin, isoniazid, and streptomycin resistant Mtb strains. The results suggest that quinoline-isoxazole-based anti-TB compounds are promising leads for new TB drug development.

  DOI：

  10.1021/jm900003c
• 作为产物：
  描述：

  7-（三氯甲基）-4-羟基喹啉 、 3-溴丙炔 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以23%的产率得到4-(2-propyn-1-yloxy)-7-(trifluoromethyl)quinoline
  参考文献：
  名称：

  Structure−Activity Relationships for a Series of Quinoline-Based Compounds Active against Replicating and Nonreplicating Mycobacterium tuberculosis

  摘要：

  Tuberculosis (TB) remains as a global pandemic that is aggravated by a lack of health care, the spread of HIV, and the emergence of multidrug-resistant TB (MDR-TB) and extensively drug-resistant TB (XDR-TB) strains. New anti-TB drugs are urgently required to shorten the long 6-12 month treatment regimen and to battle drug-resistant Mtb strains. We have identified several potent quinoline-based anti-TB compounds, bearing an isoxazole containing side-chain. The most potent compounds, 7g and 13, exhibited submicromolar activity against the replicating bacteria (R-TB), with minimum inhibitory concentrations (MICs) of 0.77 and 0.95 mu M, respectively. In general, these compounds also had micromolar activity against the nonreplicating persistent bacteria (NRP-TB) and did not show toxicity on Vero cells up to 128 mu M concentration. Compounds 7g and 13 were shown to retain their anti-TB activity against rifampin, isoniazid, and streptomycin resistant Mtb strains. The results suggest that quinoline-isoxazole-based anti-TB compounds are promising leads for new TB drug development.

  DOI：

  10.1021/jm900003c