Synthesis of naphthofuranquinones with activity against Trypanosoma cruzi
| Autor: | Carlos Alberto De Simone, Raphael S. F. Silva, Antonio V. Pinto, Gustavo L. Santos, Maria de Carmo F. R. Pinto, Elaine Maria Frade Costa, Ursula L. T. Trindade, Daniel V. Teixeira, Solange L. de Castro, Valéria R. S. Malta |
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| Rok vydání: | 2005 |
| Předmět: |
Models
Molecular Magnetic Resonance Spectroscopy Stereochemistry Trypanosoma cruzi Crystallography X-Ray Chemical synthesis Mass Spectrometry chemistry.chemical_compound Structure-Activity Relationship Aniline Furan Drug Discovery Structure–activity relationship Animals Lapachol Trypanocidal agent Pharmacology biology Organic Chemistry Biological activity General Medicine biology.organism_classification Trypanocidal Agents chemistry Indicators and Reagents Crystallization Naphthoquinones |
| Zdroj: | European journal of medicinal chemistry. 41(4) |
| ISSN: | 0223-5234 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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