title: Studies on quinones. Part 39: Synthesis and leishmanicidal activity of acylchloroquinones and hydroquinones.
abstract: Acylhydroquinone-based compounds are attractive targets for the design of new leishmanicidal drugs. We have previously described sesquiterpene quinones and hydroquinones series, which exhibit different degree of potency against Leishmania amazonensis. The present study details the preparation of acylchloroquinones and hydroquinones possessing lipophilic substituents and examines their in vitro activity against intracellular L. amazonensis amastigotes. The quinone or hydroquinone nucleus is essential for the activity of the members of the series. The lipophilicity of the cycloaliphatic systems in these members seems to attenuate the cytotoxical effect and increases the selectivity of those compounds containing the norbornene system.
authors.affiliation: Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago 22, Chile. jvalderr@puc.cl
authors.forename: Jaime A
authors.initials: JA
authors.lastname: Valderrama
authors.forename: Carlos
authors.initials: C
authors.lastname: Zamorano
authors.forename: M Florencia
authors.initials: MF
authors.lastname: González
authors.forename: Eric
authors.initials: E
authors.lastname: Prina
authors.forename: Alain
authors.initials: A
authors.lastname: Fournet
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000494:pharmacology; D005260:Female; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D007894:Leishmania mexicana / Q000187:drug effects*; D008264:Macrophages / Q000469:parasitology; D051379:Mice; D008807:Mice, Inbred BALB C; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000981:Antiprotozoal Agents; D006873:Hydroquinones; D011809:Quinones