title: Synthesis and biological activity of esters in the trans-1,2-dihydroxy-1,2-dihydroacronycine series.
abstract: Permanganate oxidation of acronycine (1) led to keto alcohol 4 which could be reduced to trans-1,2-dihydroxy-1,2-dihydroacronycine (3) using NaBH4. Acylation of 3 afforded 12, 13, and 14. These esters (12, 13, and 14) were more potent than 1 when tested against L-1210 cells in vitro. Diacetate 12 was evaluated in vivo against murine P-388 leukemia and was markedly active at a dose 16-fold lower than acronycine itself. Comparison of these results with those recently obtained in the cis-1,2-dihydroxy-1,2-dihydroacronycine series is discussed.
authors.affiliation: Laboratory of Pharmacognosy, University of Athens, Greece.
authors.forename: P
authors.initials: P
authors.lastname: Magiatis
authors.forename: S
authors.initials: S
authors.lastname: Mitaku
authors.forename: A L
authors.initials: AL
authors.lastname: Skaltsounis
authors.forename: F
authors.initials: F
authors.lastname: Tillequin
authors.forename: M
authors.initials: M
authors.lastname: Koch
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* / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology; D002453:Cell Cycle / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D007939:Leukemia L1210 / Q000188:drug therapy; D007941:Leukemia P388 / Q000188:drug therapy; D051379:Mice; D010946:Plants, Medicinal / Q000737:chemistry*; D014407:Tumor Cells, Cultured
chemical_list: C111686:1,2-dihydroxy-1,2-dihydroacronycine; D000972:Antineoplastic Agents, Phytogenic; D000175:Acronine