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Photooxidation products of primaquine Structure, antimalarial activity and hemolytic effects
Author(s) -
Brossi Arnold,
Gessner Wieslaw,
Hufford Charles D.,
Baker John K.,
Homo Frederic,
Millet Pascal,
Landau Irène
Publication year - 1987
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(87)80513-6
Subject(s) - primaquine , methemoglobin , chemistry , quinone , methemoglobinemia , malaria , stereochemistry , hemoglobin , biochemistry , chloroquine , biology , immunology
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.