Potential Antimalarials. XIX. Syntheses and Testing of α-(Piperidin-2-yl)-α-(7′-trifluoromethylquinolin-4′-yl)methanol and α-(7-Bromo-1,5-naphthyridin-4-yl)-α-(piperidin-2′-yl)methanol

Abstract

The synthesis of the mefloquine analogue α-(piperidin-2-yl)-α-(7′-trifluoromethylquinolin-4′-yl)methanol (1) from 4-bromo-7-trifluoromethylquinoline and N-(hex-5-enyl) phthalimide through N-{4-[3′-(7″-trifluoromethylquinolin-4″-yl)oxiran-2′-yl]butyl} phthalimide 1′-oxide is reported. α-(7-Bromo-1,5-naphthyridin-4-yl)-α-(piperidin-2′-yl)methanol (2) was prepared by similar procedures. In tests against the K-1 isolate of Plasmodium falciparum, compound (1) proved the more active (IC50 99 nM ).