5-oxo-N-(4-nitrophenyl)-2,3-dihydroimidazo[1,2-b]isoquinoline-1(5H)-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5-oxo-N-(4-nitrophenyl)-2,3-dihydroimidazo[1,2-b]isoquinoline-1(5H)-carboxamide
• 英文别名: 1-[(4-nitrophenyl)carbamoyl]-2,2-b]isoquinoline-5(1H)-one；N-(4-nitrophenyl)-5-oxo-2,3-dihydroimidazo[1,2-b]isoquinoline-1-carboxamide
• 化学式: C₁₈H₁₄N₄O₄
• 分子量: 350.334
• InChiKey: JMQHQOXDGWMUTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-硝基苯甲酰氯 在 sodium azide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 8.0h， 生成 5-oxo-N-(4-nitrophenyl)-2,3-dihydroimidazo[1,2-b]isoquinoline-1(5H)-carboxamide
  参考文献：
  名称：

  Antimalarial activity of novel imidazoisoquinolinone derivatives correlates with heme binding affinity

  摘要：

  A series of novel imidazoisoquinolinone derivatives were synthesized and evaluated for in vitro antimalarial efficacy against chloroquine sensitive GHA strain of Plasmodium falciparum. Compounds 2, 4, 6, 9, and 17 revealed moderate to good activities in the micromolar range. Binding interaction between these active compounds and heme were determined and correlated with antimalarial activity. A good correlation (r = 0.98) was observed between antimalarial activity and the heme dissociation constants (K (d)). These suggest that antimalarial mode of action of this class of compounds appears to be similar to that of chloroquine and involves the inhibition of hemozoin formation.

  DOI：

  10.1007/s00044-014-1231-6

文献信息

• Antimalarial activity of novel imidazoisoquinolinone derivatives correlates with heme binding affinity
  作者：Mariela Bollini、Juan J. Casal、Silvia E. Asís、Emilse S. Leal、Ana M. Bruno

  DOI：10.1007/s00044-014-1231-6

  日期：2015.4

  A series of novel imidazoisoquinolinone derivatives were synthesized and evaluated for in vitro antimalarial efficacy against chloroquine sensitive GHA strain of Plasmodium falciparum. Compounds 2, 4, 6, 9, and 17 revealed moderate to good activities in the micromolar range. Binding interaction between these active compounds and heme were determined and correlated with antimalarial activity. A good correlation (r = 0.98) was observed between antimalarial activity and the heme dissociation constants (K (d)). These suggest that antimalarial mode of action of this class of compounds appears to be similar to that of chloroquine and involves the inhibition of hemozoin formation.