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Amodiaquine N‐oxides and other 7‐chloro‐4‐aminoquinoline n‐oxides
Author(s) -
Elslager Edward F.,
Gold Eva H.,
Tendick Frank H.,
Werbel Leslie M.,
Worth Donald F.
Publication year - 1964
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570010102
Subject(s) - amodiaquine , chemistry , phenol , oxide , medicinal chemistry , aqueous solution , organic chemistry , malaria , chloroquine , immunology , biology
Oxidation of amodiaquine with perbenzoic acid gave amodiaquine N‐α‐oxide, whereas N 4 ‐methylamodiaquine and amodiaquine 1‐oxide afforded N 4 ‐methylamodiaquine N‐α,1‐dioxide and amodiaquine N‐α, 1‐dioxide, respectively. Amodiaquine 1‐oxide, O ‐methyl‐amodiaquine 1‐oxide, oxychloroquine 1‐oxide, and a variety of other 4 ‐ (7‐chloro‐4‐quinolylamino)‐α‐dialkylamino‐ o ‐cresol 1‐oxides and 7‐chloro‐4‐[(mono‐ and dialkylamino)‐alkylamino]quinoline 1‐oxides were prepared by the condensation of 4, 7‐dichloroquinoline 1‐oxide with a 4‐amino‐α‐(dialkylamino)‐ o ‐cresol, N‐α, N‐α‐diethyl‐6‐methoxytoluene‐α, ‐3‐diamine, or a mono‐ or dialkylaminoalkylamine in phenol or aqueous ethanol. N 4 ‐Methyl‐amodiaquine was synthesized from p ‐ [(7‐chloro‐4‐quinolyl)methylamino]phenol, diethyl‐amine, and paraformaldehyde. Many of the N‐oxides are highly active against the plasmodia of malaria.