Abstract
Four new naphthofuranquinones, obtained from 2-hydroxy-3-allyl-naphthoquinone ( 1) and nor-lapachol ( 2), have their structures established by physical and X-ray analysis and their activity evaluated against Trypanosoma cruzi. Compounds 3 and 4 were obtained by addition of iodine to 1 followed by cyclization generating a furan ring. Compound 5 was obtained through the acid-catalyzed reaction by dissolution of 1 in sulfuric acid. Compound 6 was synthesized by addition of bromine and aniline to 2. The IC 50/24 h for 3– 6 in assays with T. cruzi trypomastigotes was between 157 and 640 μM, while the value for crystal violet was 536.0 ± 3.0 μM. Compounds 3– 5 also inhibited epimastigote proliferation. The trypanocidal activity of the new naphthofuranquinones endowed with redox properties reinforces a rational approach in the chemotherapy of Chagas' disease.
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