(1E)-7-chloro-3-(3,4-dichlorophenyl)-1-[2-(diethylamino)ethoxyimino]-10-hydroxy-3,4-dihydro-2H-acridin-9-one | 144128-30-3

• 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: (1E)-7-chloro-3-(3,4-dichlorophenyl)-1-[2-(diethylamino)ethoxyimino]-10-hydroxy-3,4-dihydro-2H-acridin-9-one
• CAS: 144128-30-3
• 化学式: C₂₅H₂₆Cl₃N₃O₃
• 分子量: 522.859
• InChiKey: JNNXNBLIENMIHA-XHLNEMQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7-氯-3-(3,4-二氯苯基)-3,4-二氢-10-羟基-1,9-(2H,10H)-吖啶二酮 、 O-beta-二乙基氨基乙基羟胺 以 乙醇 为溶剂， 反应 1.5h， 以87%的产率得到(1E)-7-chloro-3-(3,4-dichlorophenyl)-1-[2-(diethylamino)ethoxyimino]-10-hydroxy-3,4-dihydro-2H-acridin-9-one
  参考文献：
  名称：

  Antimalarial drugs. 64. Synthesis and antimalarial properties of 1-imino derivatives of 7-chloro-3-substituted-3,4-dihydro-1,9(2H,10H)-acridinediones and related structures

  摘要：

  To improve upon the activity and properties of the 3-aryl-7-chloro-3,4-dihydro-1,9(2H,10H)-acridinediones, a variety of 1-[(alkylamino)alkylene]imino derivatives (3) were prepared and shown to be highly active antimalarial agents in both rodents and primates. Among structural modifications prepared, including N-10-alkyl and C2-substituted analogs, removal of the C-9 oxygen, and introduction of an imino side chain at C-9, the imines of the N-10-H acridinediones were the most active compounds obtained. The [3-(NN-dimethylamino)propyl]imino derivative of 7-chloro-3-(2,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione (9aa) proved to be highly active in advanced studies in primates.

  DOI：

  10.1021/jm00097a001