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Synthesis 2005(19): 3202-3208  
DOI: 10.1055/s-2005-918437
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Novel Synthetic Route to Cytotoxic 1,4-Anthraquinones from 1,4-Benzoquinones

Mª Angeles Castro*a, José Mª Miguel del Corrala, Marina Gordalizaa, Pablo A. Garcíaa, Ana Mª Gamitoa, Simone A. Gualbertob, Ronan Batistab, Arturo San Felicianoa
a Departamento de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, 37007 Salamanca, Spain
b Faculdade de Farmácia, Dpto. Productos Farmacêuticos, Universidade Federal de Minas Gerais, Cep. 30180, 112 Belo Horizonte-MG, Brazil
Fax: +34(9230)294515; e-Mail: macg@usal.es;
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Publication History

Received 14 April 2005
Publication Date:
27 October 2005 (online)

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Abstract

A new procedure to obtain anthracene-1,4-diones from p-benzoquinones and myrcene, in the presence of acids, is described. The cycloaddition reaction between α-myrcene and p-benzoquinones, followed by oxidation, led to 1,4-naphthoquinones or 1,4-anthraquinones depending upon whether the Lewis acid used in the Diels-Alder reaction, was present or absent during oxidation; furthermore, traces of acid in the solvents played an important role in determining the cycloadduct obtained. The quinones synthesized exhibited cytotoxicity towards several tumor cell lines.

Key words

1,4-naphthoquinones - anthracene-1,4-diones - 1,4-anthraquinones - Diels-Alder addition - cytotoxicity