Primaquine analogues: derivatives of 4-amino-2-methoxyacridine

Based on the antimalarial activity of primaquine (1a) and its 4-methyl analogue 1b, 4-aminoacridinyl analogues, 4-[(4-amino-1-methylbutyl)amino]-2-methoxyacridine (2a) and 4-[(4-amino-1-methylbutyl)amino]-2-methoxy-9-methylacridine (2b), were prepared and evaluated as potential tissue schizonticidal agents. These compounds were found to be substantially less active than primaquine against Plasmodium cynomolgi in the rhesus monkey. The antileishmanial activity in hamsters of 4-[[6-(diethylamino)hexyl]amino]-2-methoxy-9-methylacridine (2d) was found to be considerably less than that of 8-[[6-(diethylamino)hexyl]amino]-6-methoxy-4-methylquinoline (1c).