Synthesis and cytotoxic activity of pyranocarbazole analogues of ellipticine and acronycine.
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.
Tran-Thi
Hong Anh
HA
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.
Nguyen-Thi
Thuan
T
Michel
Sylvie
S
Tillequin
Francois
F
Koch
Michel
M
Pfeiffer
Bruno
B
Pierré
Alain
A
Trinh-Van-Dufat
Hanh
H
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*
D000970:Antineoplastic Agents; D002227:Carbazoles; D004611:Ellipticines; D011714:Pyrans; C034192:ellipticine; D000175:Acronine