POTENTIAL ANTIMALARIALS .12. 4-CHLORO-3-(SUBSTITUTED AMINO)METHYL-5-[7-BROMO (AND 7-TRIFLUOROMETHYL)-1,5-NAPHTHYRIDIN-4-YLAMINO]BIPHENYL-2-OLS AND 4-CHLORO-3-(SUBSTITUTED AMINO)METHYL-5-(7-TRIFLUOROMETHYL-QUINAZOLIN-4-YLAMINO)BIPHENYL-2-OLS

The mono-Mannich bases 3-(t-butylamino)methyl-4′-chloro-, 3-(4-benzylpiperidin-1-yl)methyl- 4′-chloro-, 3-(4-benzylpiperazin-l-yl)methyl-4′-chloro-, 4′-chloro-3-diethylaminomethyl-, 4′- chloro-3-(pyrrolidin-l-yl)methyI-, 4′-chloro-3-(piperidin-l-yl)methyl- and 4′-chloro-3-(3- and 4- methylpiperidin-l-yl)methyT5-[7-bromo (and 7-trifluoromethyl)-l, 5-naphthyridin-4-ylamino]- biphenyl-2-ol, and the corresponding substituted 5-(7-trifluoromethylquinazolin-4-ylamino)bi- phenyl-2-ols, have been prepared by condensation of the 5-amino-3-(N-substituted aminomethyl)-4′-chlorobiphenyl-2-ols and the appropriate 4-chloro heterocycle. The antimalarial activity of these products against the chloroquine-sensitive isolate (Fcq-27) of Plasmodium falciparum revealed that the 1, 5-naphthyridines reported here were less active than the corresponding di-Mannich bases, e.g. (6), derived from 4-[7-bromo (and 7-trifluoromethyl)-l′, 5′-naphthyridin-4′-ylamino]phenol, a feature not shared by the corresponding quinazolines. © 1990 ASEG.