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A striking difference in antimalarial activity between the diastereomers of 6-bromo-alpha-[2-(1-methylpiperidyl)]-9-phenanthrenemethanol, alpha-(3-peperidyl)-3,6-bis(trifluoromethyl)-9-phenanthrenemethanol, and alpha-(3-piperidyl)-2,8-bis(trifluoromethyl)-4-quinolinemethanol was observed. A possible explanation involving the N-O distance and active site binding requirements is suggested.

Three analogues of the causal prophylactic antimalarial primaquine were prepared and their antimalarial activity was evaluated. 8-[(1-Ethyl-4-aminobutyl)amino]-6-methoxy-4-methylquinoline (2a) demonstrated activity against Plasmodium berghei in mice at 20 mg/kg, with all animals cured at 320 mg/kg, and is without toxicity at 640 mg/kg. It also possessed outstanding causal prophylactic activity against Plasmodium cynomolgi in rhesus monkeys at very low dosages.