title: Synthesis and cytotoxic activity of acronycine derivatives modified at the pyran ring.
abstract: Nitration of acronycine (1) and 6-demethoxyacronycine (3) afforded 2-nitroacronycine (2) and 2-nitro-6-demethoxyacronycine (4), respectively. Reduction of 2-nitroacronycine yielded, depending on the conditions, 2-nitro-1,2-dihydroacronycine (5), 2-oxo-1,2-dihydroacronycine oxime (7) or 2-amino-1,2-dihydroacronycine (6). This latter was readily converted into 2-dimethylamino-1,2-dihydroacronycine (8), 2-acetylamino-1,2-dihydro-acronycine (9) and 2-benzoylamino-1,2-dihydroacronycine (10). The cytotoxicity of these compounds was evaluated against L1210 leukemia cells. Compounds 2 and 7 were 300- and 10-fold more potent than acronycine in inhibiting L1210 cell proliferation, respectively. Compound 2 was devoid of antitumor activity against P388 leukemia and C38 colon adenocarcinoma.
authors.forename: A
authors.initials: A
authors.lastname: Elomri
authors.forename: A L
authors.initials: AL
authors.lastname: Skaltsounis
authors.forename: S
authors.initials: S
authors.lastname: Michel
authors.forename: F
authors.initials: F
authors.lastname: Tillequin
authors.forename: M
authors.initials: M
authors.lastname: Koch
authors.forename: Y
authors.initials: Y
authors.lastname: Rolland
authors.forename: A
authors.initials: A
authors.lastname: Pierré
authors.forename: G
authors.initials: G
authors.lastname: Atassi
mesh_terms: D000175:Acronine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D000230:Adenocarcinoma / Q000188:drug therapy; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D003110:Colonic Neoplasms / Q000188:drug therapy; D004354:Drug Screening Assays, Antitumor; D007939:Leukemia L1210 / Q000188:drug therapy; D007941:Leukemia P388 / Q000188:drug therapy; D051379:Mice; D008815:Mice, Inbred Strains; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D000175:Acronine