title: Enantioselective synthesis and cytotoxic evaluation of 4,5-dihydro-5-[aryl(hydroxy)methyl]-3-methylidenefuran-2(3H)-ones.
abstract: A series of enantiomerically enriched 4,5-dihydro-5-[aryl(hydroxy)methyl]-3-methylidenefuran-2(3H)-ones (8) were synthesized by means of asymmetric Sharpless dihydroxylation of the 2-phosphorylated 5-aryl-pent-4-enoic acids 13, followed by Horner-Wadsworth-Emmons reaction of the resulting furanones 15 (Scheme 2). An enantiomeric excess (ee) of 20-95% was achieved for compounds 8, and their absolute configurations were determined by the Mosher ester method. Cytotoxic evaluation against L-1210 and HL-60 leukemia cell lines revealed that the target compounds 8 are active in the micromolar concentration range (Table 2). Thereby, significant differences in activity between the corresponding enantiomers were observed for the HL-60 cell line.
authors.affiliation: Institute of Organic Chemistry, Technical University of Łódź, Zeromskiego 116, PL-90-924 Łódź. tjanecki@p.lodz.pl
authors.forename: Tomasz
authors.initials: T
authors.lastname: Janecki
authors.forename: Anna
authors.initials: A
authors.lastname: Albrecht
authors.forename: Edyta
authors.initials: E
authors.lastname: Warzycha
authors.forename: Kazimierz
authors.initials: K
authors.lastname: Studzian
authors.forename: Anna
authors.initials: A
authors.lastname: Janecka
authors.forename: Urszula
authors.initials: U
authors.lastname: Krajewska
authors.forename: Marek
authors.initials: M
authors.lastname: Rózalski
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006801:Humans; D007783:Lactones / Q000737:chemistry* / Q000494:pharmacology*; D051379:Mice; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D007783:Lactones; D012717:Sesquiterpenes