Issue 11, 2011

Synthesis of new 9-hydroxy-α- and 7-hydroxy-β-pyran naphthoquinones and cytotoxicity against cancer cell lines

Abstract

A synthetic method to obtain α- and β-pyran naphthoquinones 10 and 11 with a hydroxyl substituent on the aromatic ring was developed. Two series of α- and β-pyran naphthoquinones were obtained from the 8-hydroxy-lawsone, and their anticancer properties were evaluated against four tumor cell lines. In general, the new compounds displayed good activity, possibly indicating that these compounds have increased pro-oxidant capacity. The 9-hydroxy-α-lapachone and 7-hydroxy-β-lapachone analogues of the natural products α-lapachone and β-lapachone were successfully produced by this methodology.

Graphical abstract: Synthesis of new 9-hydroxy-α- and 7-hydroxy-β-pyran naphthoquinones and cytotoxicity against cancer cell lines

Supplementary files

Article information

Article type
Paper
Submitted
07 Feb 2011
Accepted
07 Mar 2011
First published
08 Mar 2011

Org. Biomol. Chem., 2011,9, 4315-4322

Synthesis of new 9-hydroxy-α- and 7-hydroxy-β-pyran naphthoquinones and cytotoxicity against cancer cell lines

D. R. da Rocha, A. C. G. de Souza, J. A. L. C. Resende, W. C. Santos, E. A. dos Santos, C. Pessoa, M. O. de Moraes, L. V. Costa-Lotufo, R. C. Montenegro and V. F. Ferreira, Org. Biomol. Chem., 2011, 9, 4315 DOI: 10.1039/C1OB05209H

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