Synthesis and Antimalarial Properties of 1-Imino Derivatives of 7-Chloro-3-substituted-3,4-dihydro-1,9(2H,10H)-acridinediones and Related Structures

Article abstract of DOI:10.1021/jm00097a001

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 N₁₀-alkyl and C₂-substituted analogs, removal of the C₉ oxygen, and introduction of an imino side chain at C₉, the imines of the N₁₀-H acridinediones were the most active compounds obtained.The <3-(N,N-dimethylamino)propyl>imino derivative of7-chloro-3-(2,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione (9aa) proved to be highly active in advanced studies in primates.