5-(benzyloxy)-2-((4-(7-chloroquinolin-4-ylamino)butylamino)methyl)-1-cyclopropylpyridin-4(1H)-one | 1620023-80-4

• 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-((4-(7-chloroquinolin-4-ylamino)butylamino)methyl)-1-cyclopropylpyridin-4(1H)-one
• 英文别名: 2-[[4-[(7-Chloroquinolin-4-yl)amino]butylamino]methyl]-1-cyclopropyl-5-phenylmethoxypyridin-4-one；2-[[4-[(7-chloroquinolin-4-yl)amino]butylamino]methyl]-1-cyclopropyl-5-phenylmethoxypyridin-4-one
• CAS: 1620023-80-4
• 化学式: C₂₉H₃₁ClN₄O₂
• 分子量: 503.044
• InChiKey: SSGFFPVBFUTSGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  5.0
• 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-((4-(7-chloroquinolin-4-ylamino)butylamino)methyl)-1-cyclopropylpyridin-4(1H)-one 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以58%的产率得到2-((4-(7-chloroquinolin-4-ylamino)butylamino)methyl)-1-cyclopropyl-5-hydroxypyridin-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 碳酸氢钠 、 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-((4-(7-chloroquinolin-4-ylamino)butylamino)methyl)-1-cyclopropylpyridin-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.