7-Chloro-10-hydroxy-3-pyridin-4-yl-3,4-dihydro-2H,10H-acridine-1,9-dione | 75618-37-0

• 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: 7-Chloro-10-hydroxy-3-pyridin-4-yl-3,4-dihydro-2H,10H-acridine-1,9-dione
• 英文别名: 7-Chloro-3,4-dihydro-10-hydroxy-3-[4-pyridinyl]-1,9(2H,10H)-acridinedione；7-chloro-10-hydroxy-3-pyridin-4-yl-3,4-dihydro-2H-acridine-1,9-dione
• CAS: 75618-37-0
• 化学式: C₁₈H₁₃ClN₂O₃
• 分子量: 340.766
• InChiKey: QSRZPPVTLUHVOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-Chloro-10-hydroxy-3-pyridin-4-yl-3,4-dihydro-2H,10H-acridine-1,9-dione 、 N,N-二甲基-1,3-二氨基丙烷 以 乙醇 为溶剂， 反应 1.5h， 以89%的产率得到7-Chloro-1-[(E)-3-dimethylamino-propylimino]-10-hydroxy-3-pyridin-4-yl-1,3,4,10-tetrahydro-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
• 作为产物：
  描述：

  5-吡啶-4-基环己烷-1,3-二酮 、 邻硝基苯甲醛 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 以65%的产率得到7-Chloro-10-hydroxy-3-pyridin-4-yl-3,4-dihydro-2H,10H-acridine-1,9-dione
  参考文献：
  名称：

  Duerckheimer; Raether; Seliger, Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 7, p. 1041 - 1046

  摘要：

  DOI：

文献信息

• Duerckheimer; Raether; Seliger, Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 7, p. 1041 - 1046
  作者：Duerckheimer、Raether、Seliger、Seidenath

  DOI：——

  日期：——
• 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
  作者：Stephen J. Kesten、Margaret J. Degnan、Jocelyn Hung、Dennis J. McNamara、Daniel F. Ortwine、Susan E. Uhlendorf、Leslie M. Werbel

  DOI：10.1021/jm00097a001

  日期：1992.9

  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.