title: Synthesis and biological evaluation of indoloquinolines and pyridocarbazoles: a new example of unexpected photoreduction accompanying photocyclization.
abstract: Indoloquinoline alkaloid cryptolepine and pyridocarbazole alkaloid ellipticine are of great interest because in vitro and in vivo studies revealed their good cytotoxic properties. In order to obtain some biologically active analogs of these compounds, we developed a synthesis based on the photocyclization of tertiary N-substituted enaminones derived from 1,3-cyclohexandione and 3 or 6-aminoquinoline. The angular cyclized compounds thus obtained were tested in vitro on K 562 cells and A 2780 doxorubicin sensitive and resistant cells. All compounds were less effective than doxorubicin in sensitive cells but their activity wasn't decreased by MDR resistance.
authors.affiliation: Laboratoire de Chimie Organique Pharmaceutique, EA 2414, Faculté de Pharmacie, Montpellier, France.
authors.forename: Pierre-Jean
authors.initials: PJ
authors.lastname: Aragon
authors.forename: Ange-Désiré
authors.initials: AD
authors.lastname: Yapi
authors.forename: Frédéric
authors.initials: F
authors.lastname: Pinguet
authors.forename: Jean-Michel
authors.initials: JM
authors.lastname: Chezal
authors.forename: Jean-Claude
authors.initials: JC
authors.lastname: Teulade
authors.forename: Yves
authors.initials: Y
authors.lastname: Blache
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology*; D000903:Antibiotics, Antineoplastic / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D003500:Cyclization; D004317:Doxorubicin / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D004611:Ellipticines / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D007202:Indicators and Reagents; D020014:K562 Cells; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010777:Photochemistry; D014466:Ultraviolet Rays