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Synthesis of potential antimalarials

1970; Wiley; Volume: 7; Issue: 3 Linguagem: Inglês

10.1002/jhet.5570070321

1943-5193

John P. Schaefer, Kopal Kulkarni, Rentzea Costin, John Higgins, Linda M. Honig,

Multicomponent Synthesis of Heterocycles

Abstract A series of quinoline derivatives containing a 2‐thienyl ring in the 2‐position and CO 2 H, CH 2 OH, CHO, CH(OH)CN, CH(OH)CO 2 H, CO 2 C 2 H 5 , COCH[N(C 2 H 5 ) 2 ]CO 2 C 2 H 5 , COCH 2 N(C 2 H 5 ) 2 , COCH 3 , magnified image substituents in the 4‐position was synthesized. Both intermediate and target compounds were tested for antimalarial activity. A second series with a 5‐bromo‐2‐thienyl group in the 2‐position and CHOHCH 2 N(C 2 H 5 ) 2 , CHOHCH 2 N(CH 2 ) 6 , and CHOHCH 2 N(CH 2 C 6 H 5 ) 2 substituents in the 4‐position was also prepared, it was found that, although these quinoline methanols were moderately active antimalarials, they exhibited a high degree of phototoxicity. A third series of compounds with 2‐alkyl substituents (methyl, t ‐butyl) was also synthesized, and these were found to combine a modest degree of antimalarial activity with low phototoxicity. Several novel synthetic routes to the above compounds were developed and are detailed.