title: Synthesis and antitumor evaluation of 6-aryl-substituted benzo[j]phenanthridine- and benzo[g]pyrimido[4,5-c]isoquinolinequinones.
abstract: A variety of novel 6-arylsubstituted benzo[j]phenanthridine- and benzo[g]-pyrimido[4,5-c]isoquinolinequinones were synthesized from 1,4-naphthoquinone, aryl-aldehydes and enaminones via a two-step synthetic approach. The cytotoxic activity of the aminoquinone derivatives was evaluated in vitro against one normal cell line (MRC-5 lung fibroblasts) and three human cancer cell lines (AGS human gastric adenocarcinoma; SK-MES-1 human lung cancer cells, and J82 human bladder carcinoma) in 72-h drug exposure assays using the MTT colorimetric method. Structure-activity relationships within the series of angular quinones reveal that the insertion of pyrrol-2-yl and furan-2-yl groups at the 6-position is more significant for the increase of the potency and selectivity index of the pharmacophores.
authors.affiliation: Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile.
authors.forename: Jennyfer
authors.initials: J
authors.lastname: Iribarra
authors.forename: David
authors.initials: D
authors.lastname: Vásquez
authors.forename: Cristina
authors.initials: C
authors.lastname: Theoduloz
authors.forename: Julio
authors.initials: J
authors.lastname: Benites
authors.forename: David
authors.initials: D
authors.lastname: Ríos
authors.forename: Jaime A
authors.initials: JA
authors.lastname: Valderrama
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D016227:Benzoquinones / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D002460:Cell Line; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D016227:Benzoquinones; D010617:Phenanthridines