Synthesis and evaluation as antitumor agents of 1,4-naphthohydroquinone derivatives conjugated with amino acids and purines

We report on the synthesis of two series of 1,4-naphthohydroquinone derivatives conjugated with amino acids (Gly, Ala, Phe, and Glu) and with substituted purines linked by an aliphatic chain. The compounds were obtained through Diels-Alder cycloaddition between myrcene and 1,4-benzoquinone and evaluated in vitro for their cytotoxicity (GI50) against cultured human cancer cells of A-549 lung carcinoma, HT-29 colon adenocarcinoma, and MCF-7 breast carcinoma. The GI50 values found for some hydroquinone-amino acid and hydroquinone-purine hybrids against MCF-7 are in an activity range comparable to that of the reference drug doxorubicin.Funded by: “Comisión Nacional de Investigación Científica y Tecnológica”, CONICYT (Project FONDECYT 1060447), “Dirección de Investigación de la Vicerrectoría de Investigación y Estudios Avanzados de la Pontificia Universidad Católica de Valparaíso”, Chile (Project DII 125.796/2006) and “Junta de Castilla y León”, Spain (SA028A10-2) and European CommissionPeer Reviewe