title: Synthesis and cytotoxic evaluation of beta-alkyl or beta-aryl-delta-methyl-alpha-methylene-delta-lactones. Comparison with the corresponding gamma-lactones.
abstract: We present a simple and general strategy for the synthesis of beta,delta-disubstituted-alpha-methylene-delta-lactones starting from easily available tert-butyl 2-(diethoxyphosphoryl)alk-2-enoates. The elaborated synthetic protocol includes pyrrolidine-catalyzed Michael addition of acetone, diastereoselective reduction of the carbonyl group, lactonization and finally the Horner-Wadsworth-Emmons reaction with formaldehyde. All alpha-methylene-delta-lactones were evaluated in vitro against mouse leukemia cell line L-1210 and two human leukemia cell lines HL-60 and NALM-6. Comparison of cytotoxic activity with corresponding alpha-methylene-gamma-lactones is also discussed.
authors: Institute of Organic Chemistry, Technical University of Lodz, Zeromskiego 116, 90-924 Łódź, Poland.
authors: Lukasz
authors: L
authors: Albrecht
authors: Jakub
authors: J
authors: Wojciechowski
authors: Anna
authors: A
authors: Albrecht
authors: Wojciech M
authors: WM
authors: Wolf
authors: Anna
authors: A
authors: Janecka
authors: Kazimierz
authors: K
authors: Studzian
authors: Urszula
authors: U
authors: Krajewska
authors: Marek
authors: M
authors: Rózalski
authors: Tomasz
authors: T
authors: Janecki
authors: Henryk
authors: H
authors: Krawczyk
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051379:Mice; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D007783:Lactones