Studies on quinones. Part 39: Synthesis and leishmanicidal activity of acylchloroquinones and hydroquinones.
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.
Valderrama
Jaime A
JA
Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago 22, Chile. jvalderr@puc.cl
Zamorano
Carlos
C
González
M Florencia
MF
Prina
Eric
E
Fournet
Alain
A
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
D000981:Antiprotozoal Agents; D006873:Hydroquinones; D011809:Quinones