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Issue 8, 2016
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Molecular hybridization as a powerful tool towards multitarget quinoidal systems: synthesis, trypanocidal and antitumor activities of naphthoquinone-based 5-iodo-1,4-disubstituted-, 1,4- and 1,5-disubstituted-1,2,3-triazoles

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Abstract

Quinonoid compounds based on 5-iodo-1,4-disubstituted-, 1,4- and 1,5-disubstituted-1,2,3-triazoles were synthesized using simple methodologies and evaluated against T. cruzi, the etiological agent of Chagas disease, and cancer cell lines PC3, HCT-116, HL-60, MDA-MB-435 and SF-295. The cytotoxic potential of the lapachones was also assayed against peripheral blood mononuclear cells (PBMC). Two compounds 6 and 12 were identified as potential hits against T. cruzi. β-Lapachone-based 1,5-disubstituted-1,2,3-triazole (12) displayed an IC50/24 h = 125.1 μM, similar to benznidazole, the standard drug. Compound 12 was also more active than the precursor β-lapachone against the cancer cell lines. These compounds acting as multitarget quinoidal systems could provide promising new leads for the development of trypanocidal and/or anticancer drugs.

Graphical abstract: Molecular hybridization as a powerful tool towards multitarget quinoidal systems: synthesis, trypanocidal and antitumor activities of naphthoquinone-based 5-iodo-1,4-disubstituted-, 1,4- and 1,5-disubstituted-1,2,3-triazoles

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Supplementary files

Article information


Submitted
18 Apr 2016
Accepted
20 May 2016
First published
23 May 2016

Med. Chem. Commun., 2016,7, 1555-1563
Article type
Research Article

Molecular hybridization as a powerful tool towards multitarget quinoidal systems: synthesis, trypanocidal and antitumor activities of naphthoquinone-based 5-iodo-1,4-disubstituted-, 1,4- and 1,5-disubstituted-1,2,3-triazoles

S. B. B. B. Bahia, W. J. Reis, G. A. M. Jardim, F. T. Souto, C. A. de Simone, C. C. Gatto, R. F. S. Menna-Barreto, S. L. de Castro, B. C. Cavalcanti, C. Pessoa, M. H. Araujo and E. N. da Silva Júnior, Med. Chem. Commun., 2016, 7, 1555
DOI: 10.1039/C6MD00216A

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