Enantioselective synthesis and cytotoxic evaluation of 4,5-dihydro-5-[aryl(hydroxy)methyl]-3-methylidenefuran-2(3H)-ones |
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Authors: | Janecki Tomasz Albrecht Anna Warzycha Edyta Studzian Kazimierz Janecka Anna Krajewska Urszula Rózalski Marek |
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Institution: | Institute of Organic Chemistry, Technical University of ?ód?, Zeromskiego 116, PL-90-924 ?ód?. tjanecki@p.lodz.pl |
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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. |
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