title: Synthesis and cytotoxic activity of pyranocarbazole analogues of ellipticine and acronycine.
abstract: Various 2,2,5,11-tetramethyl- and 2,2,5,6,11-pentamethyl-2,6-dihydropyrano[3,2-b]carbazole derivatives were synthesized by condensation of 3-methylbut-2-enal or 3-chloro-3-methylbut-1-yne with an appropriate hydroxycarbazole. These compounds associate the tricyclic system responsible for the intercalating properties of ellipticine related drugs, with the dimethylpyran pharmacophore of acronycine derivatives. The study of the biological properties of the new pyrano[3,2-b]carbazole derivatives was carried out in vitro on L1210 murine leukaemia cell line. The three (+/-)-cis-diol diesters 15, 16, and 18 were the most active compounds.
authors.affiliation: Laboratoire de Pharmacognosie de l'Université René Descartes, U.M.R. / C.N.R.S. N degrees 8638, Faculté des Sciences Pharmaceutiques et Biologiques, Paris, France.
authors.forename: Hong Anh
authors.initials: HA
authors.lastname: Tran-Thi
authors.forename: Thuan
authors.initials: T
authors.lastname: Nguyen-Thi
authors.forename: Sylvie
authors.initials: S
authors.lastname: Michel
authors.forename: Francois
authors.initials: F
authors.lastname: Tillequin
authors.forename: Michel
authors.initials: M
authors.lastname: Koch
authors.forename: Bruno
authors.initials: B
authors.lastname: Pfeiffer
authors.forename: Alain
authors.initials: A
authors.lastname: Pierré
authors.forename: Hanh
authors.initials: H
authors.lastname: Trinh-Van-Dufat
mesh_terms: D000175:Acronine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000633:toxicity*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000633:toxicity*; D002227:Carbazoles / Q000138:chemical synthesis / Q000633:toxicity*; D045744:Cell Line, Tumor; D004611:Ellipticines / Q000138:chemical synthesis / Q000633:toxicity*; D007939:Leukemia L1210 / Q000188:drug therapy / Q000473:pathology; D051379:Mice; D011714:Pyrans / Q000138:chemical synthesis / Q000633:toxicity*
chemical_list: D000970:Antineoplastic Agents; D002227:Carbazoles; D004611:Ellipticines; D011714:Pyrans; C034192:ellipticine; D000175:Acronine