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Issue 30, 2012
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Synthesis of carbohydrate-based naphthoquinones and their substituted phenylhydrazono derivatives as anticancer agents

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Abstract

A novel series of carbohydrate-based 1,2-naphthoquinones 13a–c and their substituted phenylhydrazono derivatives 14a–l were synthesized and evaluated for cytotoxicity against HL-60, MDA-MB435, HCT-116 and SF-295 cancer cell lines. The compounds 9a–c showed the best cytotoxicity profile (IC50 below 2 μM) against HL-60 and MDA-MB 435 human cells, while the hydrazone derivative 14i (IC50 HL-60 1.65 μM) was selective for leukemia when compared to the reference drug doxorubicin. None of the compounds exhibited lytic effects against mouse erythrocytes. Characterization of all compounds was confirmed by one- and two-dimensional NMR techniques (1H, 13C-APT, COSY-1H × 1H and HETCOR 1JCH) and by elemental analysis.

Graphical abstract: Synthesis of carbohydrate-based naphthoquinones and their substituted phenylhydrazono derivatives as anticancer agents

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Publication details

The article was received on 20 Jul 2012, accepted on 23 Sep 2012 and first published on 25 Sep 2012


Article type: Paper
DOI: 10.1039/C2RA21514D
Citation: RSC Adv., 2012,2, 11438-11448
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    Synthesis of carbohydrate-based naphthoquinones and their substituted phenylhydrazono derivatives as anticancer agents

    V. R. Campos, E. A. D. Santos, V. F. Ferreira, R. C. Montenegro, M. C. B. V. de Souza, L. V. Costa-Lotufo, M. O. de Moraes, A. K. P. Regufe, A. K. Jordão, A. C. Pinto, J. A. L. C. Resende and A. C. Cunha, RSC Adv., 2012, 2, 11438
    DOI: 10.1039/C2RA21514D

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