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.

Novel 6-acetyl-7-chloro-1,4-alkanonaphthalenes have been synthesized from 2,5-dihydroxy-6-chloroacetophenone. The leishmanicidal activities of these compounds and their precursors were examined.Figure optionsDownload as PowerPoint slide