STUDIES ON THE TISSUE SCHIZONTICIDE OF MALARIA PARASITE:SYNTHESIS OF DERIVATIVES OF 2-SUBSTITUTED PHENOXYPRIMAQUINE,4-METHYLPRIMAQUINE AND QUINOXALINE

2-Substituted phenoxy-, 4-methyl-6-methoxy-8-aminoquino-lines and 7-methoxy-5-aminoquinoxaline were condensed with 1-phthalimido-bromo-alkane to yield 2-substituted phenoxy-, 4-methyl-6-methoxy-8-(1-phthalimidoalkyl)-aminoquinolines(compounds7～10 and15～20) and 7-methoxy-5-(1-phthalimidoalkyl) aminoquinoxalines (28～30) which were subsequently reactedwith hydrazine hydrate to give 2-substituted phenoxy-,4-methyl-6-methoxy-8-(1-aminoalkyl)-aminoquinolines (11～14 and 22～27) and 7-methoxy-5-(1-aminoalkyl) aminoquinoxalines (31～33), respectively. The 2-substituted phenoxy-6-methoxy-8-aminoquinolines (4～6) were afforded by reduction of the corresponding 8-nitroquinolines (1～3) which were obtained by condensation of 2-chloro-6-methoxy-8-nitroquinoline and substituted phenols. Among them, compounds 25 and 24 were the most effective when evaluated in Plasmodium yoelli infected mice, no parasitemia was observed after a single oral dose of10 mg/kg.