Issue 30, 2012
From the journal:

RSC Advances

Synthesis of carbohydrate-based naphthoquinones and their substituted phenylhydrazono derivatives as anticancer agents†

Vinicius R. Campos,a   Evelyne A. dos Santos,b   Vitor F. Ferreira,a   Raquel C. Montenegro,c   Maria C. B. V. de Souza,a   Letícia V. Costa-Lotufo,b   Manoel O. de Moraes,b   Anna K. P. Regufe,a   Alessandro K. Jordão,a   Angelo C. Pinto,d   Jackson A. L. C. Resendee  and  Anna C. Cunha*a  

* Corresponding authors

a Universidade Federal Fluminense, Departamento de Química Orgânica, Programa de Pós-Graduação em Química, Outeiro de São João Batista, Niterói, RJ, Brazil

b Universidade Federal do Ceará, Departamento de Fisiologia e Farmacologia, Fortaleza, CE, Brazil

c Universidade Federal do Pará, Instituto de Ciências Biológicas, Belém, PA, Brazil

d Universidade Federal do Rio de Janeiro, Departamento de Química Orgânica, Instituto de Química-CT, Bloco A, Cidade Universitária, Rio de Janeiro, RJ, Brazil

e Universidade Federal Fluminense, Departamento de Química Inorgânica, Laboratório Regional de Difração de Raios X (LDRX), Niterói, RJ, Brazil

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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Article information

DOI
https://doi.org/10.1039/C2RA21514D
Article type
Paper
Submitted
20 Jul 2012
Accepted
23 Sep 2012
First published
25 Sep 2012

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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