Photooxidation products of primaquine. Structure, antimalarial activity and hemolytic effects.
Photooxidation of primaquine (1) and 5-hydroxyprimaquine (5) afforded a blue dye for which o-quinone structure 4 was elaborated. Similar oxidation of N-ethoxyacetylprimaquine (10) afforded o-quinone 11. Tissue schizontocidal activity of 4 and 11, and bisquinolylmethine 3 prepared earlier, showed that none of them had noteworthy antimalarial activity, but all three produced methemoglobin.
Brossi
A
A
Medicinal Chemistry Section, NIDDK, Bethesda, MD 20892.
Gessner
W
W
Hufford
C D
CD
Baker
J K
JK
Homo
F
F
Millet
P
P
Landau
I
I
D000818:Animals; D001711:Biotransformation; D002470:Cell Survival / Q000187:drug effects; D006461:Hemolysis; D008099:Liver / Q000187:drug effects; D008706:Methemoglobin; D010084:Oxidation-Reduction; D010961:Plasmodium / Q000187:drug effects; D011319:Primaquine / Q000031:analogs & derivatives / Q000633:toxicity; D013329:Structure-Activity Relationship
D008706:Methemoglobin; D011319:Primaquine