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Studies on 8‐aminoquinoline 1‐oxide antimalarial agents
Author(s) -
Johnson Judith L.,
Worth Donald F.,
Colbry Normal L.,
Werbel Leslie M.
Publication year - 1984
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.5570210434
Subject(s) - primaquine , chemistry , antimalarial agent , aminoquinolines , ring (chemistry) , combinatorial chemistry , oxide , pharmacology , drug , medicinal chemistry , stereochemistry , organic chemistry , malaria , plasmodium falciparum , chloroquine , immunology , medicine
The synthesis of N ‐oxides of 8‐aminoquinolines related to primaquine has been explored in an effort to obtain a less toxic, curative, antimalarial drug. Several side chain N ‐oxide analogs ( 2b, 3b ) were prepared as well as the ring N ‐oxide of primaquine with both amines trifluoroacetylated ( 13 ). All attempts to deblock this material failed. Trifluoroacetylation of primaquine also yielded the novel acyl analog 12 which had curative activity versus P. cynomolgi in the monkey about equal to that of primaquine.