title: Synthesis and in vitro activities of ferrocenic aminohydroxynaphthoquinones against Toxoplasma gondii and Plasmodium falciparum.
abstract: Fourteen ferrocenyl aminohydroxynaphthoquinones, analogues of atovaquone, were synthesized from the hydroxynaphthoquinone core. These novel atovaquone derivatives were tested for their in vitro activity against two apicomplexan parasites of medical importance, Toxoplasma gondii and Plasmodium falciparum, including resistant strains to atovaquone (T. gondii) and chloroquine (P. falciparum). Three of these ferrocenic atovaquone derivatives composed of the hydroxynaphthoquinone core plus an amino-ferrocenic group and an aliphatic chain with 6-8 carbon atoms were found to be significantly active against T. gondii. Moreover, these novel compounds were also effective against the atovaquone-resistant strain of T. gondii (Ato(R)).
authors.affiliation: Laboratoire de Catalyse de Lille, Groupe de Synthèses Asymétriques et Molécules Thérapeutiques, UMR CNRS 8010, ENSCL, USTL, Villeneuve d'Ascq, France.
authors.forename: Apiwat
authors.initials: A
authors.lastname: Baramee
authors.forename: Alexandra
authors.initials: A
authors.lastname: Coppin
authors.forename: Marlène
authors.initials: M
authors.lastname: Mortuaire
authors.forename: Lydie
authors.initials: L
authors.lastname: Pelinski
authors.forename: Stanislas
authors.initials: S
authors.lastname: Tomavo
authors.forename: Jacques
authors.initials: J
authors.lastname: Brocard
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D016782:Apicomplexa / Q000187:drug effects*; D001665:Binding Sites; D005296:Ferrous Compounds / Q000737:chemistry; D008956:Models, Chemical; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000494:pharmacology*; D010963:Plasmodium falciparum / Q000187:drug effects*; D014122:Toxoplasma / Q000187:drug effects*
chemical_list: D000981:Antiprotozoal Agents; D005296:Ferrous Compounds; D009285:Naphthoquinones