Potential Antimalarials. XX. Mannich Base Derivatives of 2-[7-Chloroquinolin-4-ylamino and 7-Bromo(and 7-trifluoromethyl)-1,5-naphthyridin-4-ylamino]-4-chloro(or 4- or 6-t-Butyl or 4- or 5-fluoro)phenols and 4(or 6)-t-Butyl-2-(7-trifluoromethylquinolin-4-ylamino)phenol

Abstract

Syntheses are reported for some mono- and di-Mannich base derivatives of 4-chloro-, 3- or 4-fluoro-, or 2- or 4-t-butyl-substituted 2-(7′-chloroquinolin-4′-ylamino)phenols and 2-[7′-bromo(and 7′-trifluoromethyl)-1′,5′-naphthyridin-4′-ylamino]phenols.

In tests against the FC-27 isolate of Plasmodium falciparum, the most active compound was 2-(7′-chloroquinolin-4′-ylamino)-5-fluoro-4,6-bis(piperidin-1′-ylmethyl)phenol (16) with IC₅₀ 12.2 nM.