A number of hydroxy analogues of the antimalarial drug primaquine [8-[(4-amino-1-methylbutyl)amino]-6-methoxyquinoline] were synthesized and characterized by 1H NMR and mass spectra. Several of the compounds were found to be active in forming methemoglobin in human erythrocytes, particularly in those from glucose-6-phosphate dehydrogenase (G6PD) deficient subjects. Decreased levels of glutathione (GSH) in G6PD-deficient erythrocytes were also found with compounds that were active methemoglobin formers.
Interfering ECD-sensitive peaks at short tR, from side reactions of PFB-Br, can be removed on a short silica gel column since they elute with 5% toluene in hexane and the PFB-pyrethroid derivatives can be subsequently eluted with toluene (modified from Kovác and Anderle, 1978).Pentafluorobenzylation provides a rapid and convenient method for introducing a highly ECD sensitive substituent into -cyanophenoxybenzyl pyrethroids. These PFB derivatives may be useful in confirming the identity of residues analyzed by other methods and, with a suitable cleanup procedure, in enhancing the sensitivity of residue
analysis. ACKNOWLEDGMENTWe thank Luis Ruzo, Roy Holmstead, and Ian Smith, currently or formerly of this laboratory, for advice and assistance. Edwin Friedrich of the Chemistry Department, University of California at Davis, provided helpful comments. Axel Ehman of Shell Development Company (Modesto, CA) made important suggestions on the acetone derivatization reaction. The GC/MS determinations were made at the Finnigan Corporation (Sunnyvale, CA) by courtesy of Ronald Skinner. NMR spectra were recorded at the Stanford Magnetic
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