title: Synthesis of naphthofuranquinones with activity against Trypanosoma cruzi.
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 microM, while the value for crystal violet was 536.0 +/- 3.0 microM. 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.
authors.affiliation: Núcleo de Pesquisas em Produtos Naturais, CCS, Universidade Federal do Rio de Janeiro, Brazil.
authors.forename: Raphael S F
authors.initials: RS
authors.lastname: Silva
authors.forename: Elaine M
authors.initials: EM
authors.lastname: Costa
authors.forename: Ursula L T
authors.initials: UL
authors.lastname: Trindade
authors.forename: Daniel V
authors.initials: DV
authors.lastname: Teixeira
authors.forename: Maria de Carmo F R
authors.initials: Mde C
authors.lastname: Pinto
authors.forename: Gustavo L
authors.initials: GL
authors.lastname: Santos
authors.forename: Valeria R S
authors.initials: VR
authors.lastname: Malta
authors.forename: Carlos Alberto
authors.initials: CA
authors.lastname: De Simone
authors.forename: Antonio Ventura
authors.initials: AV
authors.lastname: Pinto
authors.forename: Solange L
authors.initials: SL
authors.lastname: de Castro
mesh_terms: D000818:Animals; D003460:Crystallization; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014344:Trypanocidal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D014349:Trypanosoma cruzi / Q000187:drug effects*
chemical_list: D007202:Indicators and Reagents; D009285:Naphthoquinones; D014344:Trypanocidal Agents