title: 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.
authors.affiliation: Universidade Federal Fluminense, Departamento de Química Orgânica, Outeiro de São João Batista, s/n°, Centro, Niterói, 24020-141, Rio de Janeiro, Brazil.
authors.forename: David R
authors.initials: DR
authors.lastname: da Rocha
authors.forename: Ana C G
authors.initials: AC
authors.lastname: de Souza
authors.forename: Jackson A L C
authors.initials: JA
authors.lastname: Resende
authors.forename: Wilson C
authors.initials: WC
authors.lastname: Santos
authors.forename: Evelyne A
authors.initials: EA
authors.lastname: dos Santos
authors.forename: Cláudia
authors.initials: C
authors.lastname: Pessoa
authors.forename: Manoel O
authors.initials: MO
authors.lastname: de Moraes
authors.forename: Letícia V
authors.initials: LV
authors.lastname: Costa-Lotufo
authors.forename: Raquel C
authors.initials: RC
authors.lastname: Montenegro
authors.forename: Vitor F
authors.initials: VF
authors.lastname: Ferreira
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008958:Models, Molecular; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D001578:Benzopyrans; D009285:Naphthoquinones