The evaluation of quinonoid compounds against Trypanosoma cruzi: Synthesis of imidazolic anthraquinones, nor-β-lapachone derivatives and β-lapachone-based 1,2,3-triazoles

In continuation to our screening program of napththoquinones with activity against bloodstream trypomastigote forms of Trypanosoma cruzi, the etiological agent of Chagas’ disease, new β-lapachone-based 1,2,3-triazoles, 3-arylamino-nor-β-lapachones, 3-alkoxy-nor-β-lapachones and imidazole anthraquino...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2010-05, Vol.18 (9), p.3224-3230
Main Authors: da Silva Júnior, Eufrânio N., Guimarães, Tiago T., Menna-Barreto, Rubem F.S., Pinto, Maria do Carmo F.R., de Simone, Carlos A., Pessoa, Claudia, Cavalcanti, Bruno C., Sabino, José R., Andrade, Carlos Kleber Z., Goulart, Marilia O.F., de Castro, Solange L., Pinto, Antônio V.
Format: Article
Language:English
Subjects:
Animals
Anthraquinones - chemical synthesis
Anthraquinones - chemistry
Anthraquinones - pharmacology
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiparasitic agents
Antiparasitic Agents - chemical synthesis
Antiparasitic Agents - chemistry
Antiparasitic Agents - pharmacology
Biological and medical sciences
Chagas’ disease
Crystallography, X-Ray
Experimental chemotherapy
Imidazoles - chemical synthesis
Imidazoles - chemistry
Imidazoles - pharmacology
Medical sciences
Mice
Molecular Structure
Naphthoquinones
Naphthoquinones - chemical synthesis
Naphthoquinones - chemistry
Naphthoquinones - pharmacology
Nor-β-lapachone
Parasitic Sensitivity Tests
Pharmacology. Drug treatments
Quinones - chemical synthesis
Quinones - chemistry
Quinones - pharmacology
Triazoles - chemical synthesis
Triazoles - chemistry
Triazoles - pharmacology
Trypanosoma cruzi
Trypanosoma cruzi - drug effects
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Summary:In continuation to our screening program of napththoquinones with activity against bloodstream trypomastigote forms of Trypanosoma cruzi, the etiological agent of Chagas’ disease, new β-lapachone-based 1,2,3-triazoles, 3-arylamino-nor-β-lapachones, 3-alkoxy-nor-β-lapachones and imidazole anthraquinones were synthesized and evaluated against T. cruzi, with good results. In continuing our screening program of naphthoquinone activity against Trypanosoma cruzi, the aetiological agent of Chagas’ disease, new β-lapachone-based 1,2,3-triazoles, 3-arylamino-nor-β-lapachones, 3-alkoxy-nor-β-lapachones and imidazole anthraquinones were synthesised and evaluated against bloodstream trypomastigote forms of the parasite. Compounds 2,2-dimethyl-3-(2,4-dibromophenylamino)-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione, IC50/24h 24.9±7.4 and 4-azido-3-bromo-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione with 23.4±3.8μM showed a trypanosomicidal activity higher than benznidazole. These results demonstrate the potential of naphthoquinone derivatives as novel structures for the development of alternative drugs for Chagas’ disease.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2010.03.029