Synthesis and antileishmanial activity of 6-methoxy-4-methyl-N-[6-(substituted-1-piperazinyl)hexyl]-8-quinolinami nes and related compounds

Article abstract of DOI:10.1021/jm00356a013

The 8-quinolinamine, 4-[6-[(6-methoxy-4-methyl-8-quinolinyl)amino]hexyl]-1-piperazineethanol (1b), has been shown to be highly effective against Leishmania donovani infections in hamsters. In an effort to obtain a more potent, less toxic 8-quinolinamine, a series of analogues (2) was prepared that examined particularly the structural requirements of the terminal of the terminal piperazine moiety. Of the substituted piperazines and alternative heterocycles prepared, as well as those quinoline analogues with ring insertion of a methyl group in the 2-position or an aryloxy substituent in the 5-position, an increase in potency was achieved only with the 2-hydroxypropyl analogue (2f).