7-chloro-10-hydroxy-3-(2-methoxy-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione | 55579-56-1

• 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-(2-methoxy-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione
• 英文别名: 7-chloro-10-hydroxy-3-(2-methoxyphenyl)-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone；7-chloro-10-hydroxy-3-(2-methoxyphenyl)-3,4-dihydro-2H-acridine-1,9-dione
• CAS: 55579-56-1
• 化学式: C₂₀H₁₆ClNO₄
• 分子量: 369.804
• InChiKey: AAMVGFOFHMQYFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.8
• 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-(2-methoxy-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione 在 三氯化磷 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 2.5h， 生成 7-Chloro-1-[(E)-3-dimethylamino-propylimino]-3-(2-methoxy-phenyl)-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：

  2-methoxybenzalacetone 在 盐酸 、 sodium hydroxide 、 硫酸 、 sodium ethanolate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 16.5h， 生成 7-chloro-10-hydroxy-3-(2-methoxy-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione
  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

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：——
• US3947449A
  申请人：——

  公开号：US3947449A

  公开（公告）日：1976-03-30
• 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.