title: Synthesis, characterization and biological evaluation of some novel 17-isoxazoles in the estrone series.
abstract: Regioselective 1,3-dipolar cycloadditions of different aryl nitrile oxides to mestranol were carried out to furnish novel steroidal 17α-isoxazoles in good to excellent yields. Copper(I) was found to be an efficient catalyst, accelerating the intermolecular ring-closures and leading exclusively to 3,5-disubstituted isoxazoles. The yields of the cycloadducts, however, were influenced by the substituents on the aromatic moiety of the 1,3-dipoles. Moreover, dehydration of the primary products resulted in the corresponding Δ(16,17)exo-heterocyclic derivatives. All the synthesized compounds were subjected to in vitro pharmacological studies of their antiproliferative effects relative to three human malignant cell lines (HeLa, MCF7 and A2780).
authors.affiliation: Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
authors.forename: Dóra
authors.initials: D
authors.lastname: Kovács
authors.forename: Zalán
authors.initials: Z
authors.lastname: Kádár
authors.forename: Gergő
authors.initials: G
authors.lastname: Mótyán
authors.forename: Gyula
authors.initials: G
authors.lastname: Schneider
authors.forename: János
authors.initials: J
authors.lastname: Wölfling
authors.forename: István
authors.initials: I
authors.lastname: Zupkó
authors.forename: Eva
authors.initials: E
authors.lastname: Frank
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002384:Catalysis; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D004354:Drug Screening Assays, Antitumor; D004970:Estrone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D008656:Mestranol / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry; D010087:Oxides / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D007555:Isoxazoles; D009570:Nitriles; D010087:Oxides; D004970:Estrone; D003300:Copper; D008656:Mestranol