Synthesis of 2-ferrocenylquinoline derivatives and evaluation of their antimalarial activity

Some quinoline-based compounds bearing a ferrocenyl unit in the 2-position of the heterocyclic system were synthesized from ferrocenyl-o-nitrochalcones through a simple hydrogenation/intramolecular cyclization sequence and fully characterized. The obtained ferrocenyl derivatives were evaluated in vitro as antimalarial agents against chloroquine-susceptible D10 and chloroquine-resistant W2 strains of Plasmodium falciparum and a beneficial effect of the organometallic moiety was evidenced in comparison with the phenyl-substituted analogues. All the ferrocenyl heterocycles inhibited the parasite growth in μM range and the lowest values of IC50 were determined for derivatives containing a dimethylamino group as additional substituent.

Graphical abstractSome 2-ferrocenylquinoline derivatives were prepared by a simple hydrogenation-cyclization sequence of the corresponding nitrochalcones and tested in vitro for their antiplasmodial activity.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Novel 2-ferrocenylquinolines were prepared from the corresponding nitrochalcones. ► Quinoline-based ferrocenes were tested for their antimalarial activity. ► In comparison with phenyl analogues ferrocenylquinolines displayed lowest IC50 values.