title: Synthesis and antitumour activity of fluorinated 1-aza and 1,8-diazaanthraquinones.
abstract: A series of 3-fluoro-1-aza- and 1,8-diazaanthraquinones, structurally related to the antitumour antibiotic diazaquinomycin A, have been prepared by Diels-Alder reactions of 2-fluoro-2-propenal N, N-dimethylhydrazone and the corresponding quinones. These compounds showed potent in vitro activity against different tumour cell lines. They also showed some selectivity towards rapid-growth tumours when compared to other non-fluorinated analogues. In contrast with diazaquinomycin A, the azaanthraquinones studied here have not shown significant activity as thymidylate synthase inhibitors. Some compounds showed a high activity as inhibitors of protein, DNA and RNA biosynthesis.
authors.affiliation: Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, Madrid, Spain.
authors.forename: M T
authors.initials: MT
authors.lastname: Ramos
authors.forename: L M
authors.initials: LM
authors.lastname: Díaz-Guerra
authors.forename: S
authors.initials: S
authors.lastname: García-Copín
authors.forename: C
authors.initials: C
authors.lastname: Avendaño
authors.forename: D
authors.initials: D
authors.lastname: García-Grávalos
authors.forename: T
authors.initials: T
authors.lastname: García de Quesada
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004247:DNA / Q000096:biosynthesis; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D011500:Protein Synthesis Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D012313:RNA / Q000096:biosynthesis; D013055:Spectrophotometry, Infrared; D013940:Thymidylate Synthase / Q000037:antagonists & inhibitors; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D011500:Protein Synthesis Inhibitors; D012313:RNA; D004247:DNA; D013940:Thymidylate Synthase