title: Synthesis and in vitro antiproliferative activity of new phenylaminoisoquinolinequinones against cancer cell lines.
abstract: A variety of phenylaminoisoquinolinequinones were synthesized and tested for their antiproliferative activity against three human-tumor derived cancer cell lines. The new aminoquinones were prepared from 4-methoxycarbonyl-3-methylisoquinoline-5,8-quinone (1) via acid-induced amination and bromination reactions. Remarkable differences in antiproliferative activity were observed depending upon the location and donor capacity of the substituted phenylamino group at the quinone nucleus. The effect of the substituents on the biological activity is discussed in terms of the donor-acceptor interactions which were evaluated through the redox properties of the aminoquinones.
authors.affiliation: Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago 26094411, Chile.
authors.forename: Virginia
authors.initials: V
authors.lastname: Delgado
authors.forename: Andrea
authors.initials: A
authors.lastname: Ibacache
authors.forename: Verónica
authors.initials: V
authors.lastname: Arancibia
authors.forename: Cristina
authors.initials: C
authors.lastname: Theoduloz
authors.forename: Jaime A
authors.initials: JA
authors.lastname: Valderrama
mesh_terms: D000586:Amination; D000814:Aniline Compounds / Q000138:chemical synthesis / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001547:Benzaldehydes / Q000737:chemistry; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003437:Crotonates / Q000737:chemistry; D004354:Drug Screening Assays, Antitumor; D054879:Halogenation; D006801:Humans; D020128:Inhibitory Concentration 50; D007546:Isoquinolines / Q000737:chemistry; D010084:Oxidation-Reduction; D015363:Quinolones / Q000138:chemical synthesis / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000814:Aniline Compounds; D000970:Antineoplastic Agents; D001547:Benzaldehydes; D003437:Crotonates; D007546:Isoquinolines; D015363:Quinolones; C112784:2,5-dihydroxybenzaldehyde