1-[3-[(7-Chloroquinolin-4-yl)amino]propyl]-2-ethyl-3-phenylmethoxypyridin-4-one | 1439362-49-8

• 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-[3-[(7-Chloroquinolin-4-yl)amino]propyl]-2-ethyl-3-phenylmethoxypyridin-4-one
• 英文别名: 1-[3-[(7-chloroquinolin-4-yl)amino]propyl]-2-ethyl-3-phenylmethoxypyridin-4-one
• CAS: 1439362-49-8
• 化学式: C₂₆H₂₆ClN₃O₂
• 分子量: 447.964
• InChiKey: NCDCYGSBYYORMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[3-[(7-Chloroquinolin-4-yl)amino]propyl]-2-ethyl-3-phenylmethoxypyridin-4-one 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 6.5h， 生成 1-[3-[(7-Chloroquinolin-4-yl)amino]propyl]-2-ethyl-3-hydroxypyridin-4-one
  参考文献：
  名称：

  Synthesis, Antiplasmodial Activity, and β-Hematin Inhibition of Hydroxypyridone–Chloroquine Hybrids

  摘要：

  A series of noncytotoxic 4-aminoquinoline-3-hydroxypyridin-4-one hybrids were synthesized on the basis of a synergistic in vitro combination of a precursor N-alkyl-3-hydroxypyridin-4-one with chloroquine (CQ) and tested in vitro against CO resistant (K1 and W2). an sensitive (3D7) strains of Plasmodium falciparum. In vitro antiplasmodial activity of the precursors was negated by blocking the chelator moiety Via complexation with gallium(III) or benzyl protection. None of the precursors inhibited beta-hematin formation. Most hybrids were more potent inhibitors of beta-hematin formation than CQ and a correlation between antiplasmodial activity and inhibition of beta-hematin formation was observed. Potent hybrids against K1, 3D7, and W2, respectively, were 8c (0.13, 0.004, and 0.1 mu M); 8d (0.08, 0.01, and 0.02 mu M); and 7g (0.07, 0.03, and 0.08 mu M).

  DOI：

  10.1021/ml4001084
• 作为产物：
  描述：

  乙基麦芽酚 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 46.0h， 生成 1-[3-[(7-Chloroquinolin-4-yl)amino]propyl]-2-ethyl-3-phenylmethoxypyridin-4-one
  参考文献：
  名称：

  Synthesis, Antiplasmodial Activity, and β-Hematin Inhibition of Hydroxypyridone–Chloroquine Hybrids

  摘要：

  A series of noncytotoxic 4-aminoquinoline-3-hydroxypyridin-4-one hybrids were synthesized on the basis of a synergistic in vitro combination of a precursor N-alkyl-3-hydroxypyridin-4-one with chloroquine (CQ) and tested in vitro against CO resistant (K1 and W2). an sensitive (3D7) strains of Plasmodium falciparum. In vitro antiplasmodial activity of the precursors was negated by blocking the chelator moiety Via complexation with gallium(III) or benzyl protection. None of the precursors inhibited beta-hematin formation. Most hybrids were more potent inhibitors of beta-hematin formation than CQ and a correlation between antiplasmodial activity and inhibition of beta-hematin formation was observed. Potent hybrids against K1, 3D7, and W2, respectively, were 8c (0.13, 0.004, and 0.1 mu M); 8d (0.08, 0.01, and 0.02 mu M); and 7g (0.07, 0.03, and 0.08 mu M).

  DOI：

  10.1021/ml4001084

文献信息

• Synthesis, Antiplasmodial Activity, and β-Hematin Inhibition of Hydroxypyridone–Chloroquine Hybrids
  作者：Warren A. Andayi、Timothy J. Egan、Jiri Gut、Philip J. Rosenthal、Kelly Chibale

  DOI：10.1021/ml4001084

  日期：2013.7.11

  A series of noncytotoxic 4-aminoquinoline-3-hydroxypyridin-4-one hybrids were synthesized on the basis of a synergistic in vitro combination of a precursor N-alkyl-3-hydroxypyridin-4-one with chloroquine (CQ) and tested in vitro against CO resistant (K1 and W2). an sensitive (3D7) strains of Plasmodium falciparum. In vitro antiplasmodial activity of the precursors was negated by blocking the chelator moiety Via complexation with gallium(III) or benzyl protection. None of the precursors inhibited beta-hematin formation. Most hybrids were more potent inhibitors of beta-hematin formation than CQ and a correlation between antiplasmodial activity and inhibition of beta-hematin formation was observed. Potent hybrids against K1, 3D7, and W2, respectively, were 8c (0.13, 0.004, and 0.1 mu M); 8d (0.08, 0.01, and 0.02 mu M); and 7g (0.07, 0.03, and 0.08 mu M).