5-(benzyloxy)-2-((N-(7-chloroquinolin-4-ylamino)hexylamino)methyl)-1-methylpyridin-4(1H)-one | 1620023-76-8

• 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: 5-(benzyloxy)-2-((N-(7-chloroquinolin-4-ylamino)hexylamino)methyl)-1-methylpyridin-4(1H)-one
• 英文别名: 2-[[6-[(7-Chloroquinolin-4-yl)amino]hexylamino]methyl]-1-methyl-5-phenylmethoxypyridin-4-one；2-[[6-[(7-chloroquinolin-4-yl)amino]hexylamino]methyl]-1-methyl-5-phenylmethoxypyridin-4-one
• CAS: 1620023-76-8
• 化学式: C₂₉H₃₃ClN₄O₂
• 分子量: 505.06
• InChiKey: YHTJSIOLUBGVFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(benzyloxy)-2-((N-(7-chloroquinolin-4-ylamino)hexylamino)methyl)-1-methylpyridin-4(1H)-one 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以99%的产率得到2-((N-(7-chloroquinolin-4-ylamino)hexylamino)methyl)-5-hydroxy-1-methylpyridin-4(1H)-one trihydrogenchloride
  参考文献：
  名称：

  Kojic acid derived hydroxypyridinone–chloroquine hybrids: Synthesis, crystal structure, antiplasmodial activity and β-haematin inhibition

  摘要：

  Aminochloroquinoline-kojic acid hybrids were synthesized and evaluated for p-haematin inhibition and antiplasmodial activity against drug resistant (K1) and sensitive (3D7) strains of Plasmodium falciparum. Compound 7j was the most potent compound in both strains (IC503D7 = 0.004 mu M; IC50K1 = 0.03 mu M) and had the best beta-haematin inhibition activity (0.07 IC50 equiv vs 1.91 IC50 equiv for chloroquine). One compound 8c was found to be equipotent in both strains (IC50 = 0.04 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.012
• 作为产物：
  描述：

  4,7-二氯喹啉 在 sodium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 29.5h， 生成 5-(benzyloxy)-2-((N-(7-chloroquinolin-4-ylamino)hexylamino)methyl)-1-methylpyridin-4(1H)-one
  参考文献：
  名称：

  Kojic acid derived hydroxypyridinone–chloroquine hybrids: Synthesis, crystal structure, antiplasmodial activity and β-haematin inhibition

  摘要：

  Aminochloroquinoline-kojic acid hybrids were synthesized and evaluated for p-haematin inhibition and antiplasmodial activity against drug resistant (K1) and sensitive (3D7) strains of Plasmodium falciparum. Compound 7j was the most potent compound in both strains (IC503D7 = 0.004 mu M; IC50K1 = 0.03 mu M) and had the best beta-haematin inhibition activity (0.07 IC50 equiv vs 1.91 IC50 equiv for chloroquine). One compound 8c was found to be equipotent in both strains (IC50 = 0.04 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.012

文献信息

• Kojic acid derived hydroxypyridinone–chloroquine hybrids: Synthesis, crystal structure, antiplasmodial activity and β-haematin inhibition
  作者：Warren Andrew Andayi、Timothy J. Egan、Kelly Chibale

  DOI：10.1016/j.bmcl.2014.06.012

  日期：2014.8

  Aminochloroquinoline-kojic acid hybrids were synthesized and evaluated for p-haematin inhibition and antiplasmodial activity against drug resistant (K1) and sensitive (3D7) strains of Plasmodium falciparum. Compound 7j was the most potent compound in both strains (IC503D7 = 0.004 mu M; IC50K1 = 0.03 mu M) and had the best beta-haematin inhibition activity (0.07 IC50 equiv vs 1.91 IC50 equiv for chloroquine). One compound 8c was found to be equipotent in both strains (IC50 = 0.04 mu M). (C) 2014 Elsevier Ltd. All rights reserved.