Synthesis and antimalarial effects of 4-[(7-chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]-6-alkylphenols and their Nω-oxides

• Published in: Journal of medicinal chemistry Vol. 30; no. 5; pp. 906 - 911
• Main Authors: KESTEN, S. J, JOHNSON, J, WERBEL, L. M
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01.05.1987
• Subjects: Aminoquinolines - chemical synthesis; Aminoquinolines - therapeutic use; Animals; Chemical Phenomena; Chemistry; Cyclic N-Oxides - chemical synthesis; Cyclic N-Oxides - therapeutic use; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Malaria - drug therapy; Mice; Organic chemistry; Phenols - chemical synthesis; Phenols - therapeutic use; Plasmodium berghei; Preparations and properties; Structure-Activity Relationship; Antimalarial; Nitrogen heterocycle; Nitrone; Bicyclic compound; Phenols; Benzenic compound; Aromatic compound; Biological activity
• ISSN: 0022-2623; 1520-4804

A series of 4-[(7-chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]-6-alkylphenols and their N omega-oxides were synthesized by the condensation of 4,7-dichloroquinoline and 4,7-dichloroquinoline N omega-oxide with appropriately substituted 4-amino-2-[(diethylamino)methyl]-6-alkylphenol dihydrochlorides. The latter precursors were prepared in a six-step synthesis starting from available 2-alkylphenols. Several of the title compounds display potent antimalarial activity in mice.