6-methoxy-8-nitro-5-quinoline-4-carboxaldehyde | 98509-96-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-methoxy-8-nitro-5-quinoline-4-carboxaldehyde
• 英文别名: 6-methoxy-8-nitro-5-[3-(trifluoromethyl)phenoxy]quinoline-4-carbaldehyde
• CAS: 98509-96-7
• 化学式: C₁₈H₁₁F₃N₂O₅
• 分子量: 392.291
• InChiKey: GOXTWQRNQQQSKY-UHFFFAOYSA-N

物化性质

• 熔点：
  204-205 °C
• 沸点：
  508.3±50.0 °C(predicted)
• 密度：
  1.461±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  91.56
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-methoxy-8-nitro-5-quinoline-4-carboxaldehyde 在 氢氧化钾 、 sodium tetrahydroborate 、 tributylethylammonium iodide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 6-methoxy-4-(methoxymethyl)-8-nitro-5-quinoline
  参考文献：
  名称：

  4-Substituted 5-[m-(trifluoromethyl)phenoxy]primaquine analogs as potential antimalarial agents

  摘要：

  Five 4-substituted 5-[m-(trifluoromethyl)phenoxy]primaquine analogues were synthesized and tested for radical curative activity against Plasmodium cynomolgi in Rhesus monkeys and for blood schizonticidal antimalarial activity against Plasmodium berghei in mice. In addition, they were evaluated for causal prophylactic antimalarial activity against Plasmodium berghei yoelii in mice. One compound, 4-ethyl-5-[m-(trifluoromethyl)phenoxy]primaquine (2b), showed radical curative activity equivalent to 4-methyl-5-[m-(trifluoromethyl)phenoxy]primaquine (2a). A second compound showed radical curative activity slightly less than 2a and 2b; the remaining three compounds were not active against P. cynomolgi. All five compounds showed much higher blood schizonticidal activity and less toxicity than primaquine; however, none of the compounds were as active as 2a. Three of four compounds tested showed high activity against P. berghei yoelii.

  DOI：

  10.1021/jm00149a004
• 作为产物：
  描述：

  4-methyl-6-methoxy-8-nitro-5-quinoline 在 selenium(IV) oxide 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙酸酐 为溶剂， 以81%的产率得到6-methoxy-8-nitro-5-quinoline-4-carboxaldehyde
  参考文献：
  名称：

  4-Substituted 5-[m-(trifluoromethyl)phenoxy]primaquine analogs as potential antimalarial agents

  摘要：

  Five 4-substituted 5-[m-(trifluoromethyl)phenoxy]primaquine analogues were synthesized and tested for radical curative activity against Plasmodium cynomolgi in Rhesus monkeys and for blood schizonticidal antimalarial activity against Plasmodium berghei in mice. In addition, they were evaluated for causal prophylactic antimalarial activity against Plasmodium berghei yoelii in mice. One compound, 4-ethyl-5-[m-(trifluoromethyl)phenoxy]primaquine (2b), showed radical curative activity equivalent to 4-methyl-5-[m-(trifluoromethyl)phenoxy]primaquine (2a). A second compound showed radical curative activity slightly less than 2a and 2b; the remaining three compounds were not active against P. cynomolgi. All five compounds showed much higher blood schizonticidal activity and less toxicity than primaquine; however, none of the compounds were as active as 2a. Three of four compounds tested showed high activity against P. berghei yoelii.

  DOI：

  10.1021/jm00149a004

文献信息

• CARROLL, F. I.;BERRANG, B.;LINN, C. P., J. MED. CHEM., 1985, 28, N 11, 1564-1657
  作者：CARROLL, F. I.、BERRANG, B.、LINN, C. P.

  DOI：——

  日期：——