title: Synthesis and evaluation as antitumor agents of 1,4-naphthohydroquinone derivatives conjugated with amino acids and purines.
abstract: 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.
authors.affiliation: Facultad de Ciencias, Instituto de Química, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile.
authors.forename: Aurora
authors.initials: A
authors.lastname: Molinari
authors.forename: Alfonso
authors.initials: A
authors.lastname: Oliva
authors.forename: Claudia
authors.initials: C
authors.lastname: Ojeda
authors.forename: José M
authors.initials: JM
authors.lastname: Miguel del Corral
authors.forename: Maria A
authors.initials: MA
authors.lastname: Castro
authors.forename: Faustino
authors.initials: F
authors.lastname: Mollinedo
authors.forename: Arturo
authors.initials: A
authors.lastname: San Feliciano
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D004317:Doxorubicin / Q000494:pharmacology; D019073:HT29 Cells; D006801:Humans; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D061986:MCF-7 Cells; D015394:Molecular Structure; D011687:Purines / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D000596:Amino Acids; D000970:Antineoplastic Agents; D006873:Hydroquinones; D011687:Purines; C063601:1,4-naphthohydroquinone; D004317:Doxorubicin
keywords: Antineoplastic; Cytotoxicity; Hybrids; Hydroquinone-amino acid; Hydroquinone-purine