Synthesis of 4-alkyl- and 4-(.beta.-alkylvinyl) derivatives of primaquine as potential antimalarials

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Abstract
4-(.beta.-Alkylvinyl)-6-methoxy-8-nitroquinolines (6) were prepared from 6-methoxy-8-nitroquinoline-4-carboxaldehyde via at Wittig reaction. Stannous chloride reduction of 6 gave 4-(.beta.-alkylvinyl)-8-amino-6-methoxyquinolines (8), whereas catalytic reduction of 6 using Raney N catalyst gave 4-alkyl-8-amino-6-methoxyquinolines (7). Alkylation of 7 and 8 with 4-iodo-1-phthalimidopentane, followed by removal of the phthaloyl-protecting group with hydrazine, gave 4-alkyl and 4-(.beta.-alkylvinyl) derivatives of primiquine, respectively. These compounds were evaluated for antimalarial activity against Plasmodium berghei and P. berghei yoelii in mice and against P. cynomolgi in rhesus monkeys. Several of the compounds were active in the P. bergheii yoelii screen. None of the compounds showed significant activity in the other 2 screens.

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