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Synthesis and biological evaluation of N-alkyl naphthoimidazoles derived from β-lapachone against Trypanosoma cruzi bloodstream trypomastigotes

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Abstract

The QSAR study of 34 2-aryl-naphthoimidazoles screened so far revealed that σi is the most important factor for their lytic activity on the bloodstream trypomastigote forms of T. cruzi, the etiologic agent of Chagas disease. Based on this result, 16 new N-alkyl-naphthoimidazoles derived from 6,6-dimethyl-3,4,5,6-tetrahydrobenzo[7,8]chromene[5,6-d]imidazole (the product of the reaction of β-lapachone with paraformaldehyde) by its reaction with halo-alkanes were prepared and evaluated against the parasite and peritoneal macrophages. The N1-n-hexyl and N3-n-hexyl naphthoimidazoles were 2.2 and 3.2 times more active than the standard drug benznidazole with selectivity indices of 2.7 and 13.4, respectively.

Graphical abstract: Synthesis and biological evaluation of N-alkyl naphthoimidazoles derived from β-lapachone against Trypanosoma cruzi bloodstream trypomastigotes

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Publication details

The article was received on 08 Feb 2017, accepted on 20 Feb 2017, published on 27 Feb 2017 and first published online on 27 Feb 2017


Article type: Research Article
DOI: 10.1039/C7MD00069C
Citation: Med. Chem. Commun., 2017, Advance Article
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    Synthesis and biological evaluation of N-alkyl naphthoimidazoles derived from β-lapachone against Trypanosoma cruzi bloodstream trypomastigotes

    A. M. da Silva, L. Araújo-Silva, A. C. S. Bombaça, R. F. S. Menna-Barreto, C. E. Rodrigues-Santos, A. B. Buarque Ferreira and S. L. de Castro, Med. Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7MD00069C

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