posted on 2005-05-19, 00:00authored byTomasz Janecki, Edyta Błaszczyk, Kazimierz Studzian, Anna Janecka, Urszula Krajewska, Marek Różalski
5-Alkyl- and 5-arylalkyl-3-methylenedihydrofuran-2-ones 13a−e, 3-alkylidenedihydrofuran-2-ones 18a−c, and 3-methylenepyrrolidin-2-ones 16a−e were synthesized utilizing ethyl
2-diethoxyphosphoryl-4-nitroalkanoates 9a−e as common intermediates. All obtained compounds were tested against L-1210, HL-60, and NALM-6 leukemia cells. The highest cytotoxic
activity was observed for 3-methylenefuranones 13d,e bearing benzyl or 3,4-dimethoxyphenylmethyl substituents at position 5, with IC50 values of 5.4 and 6.0 μM, respectively. Contrary
to the literature reports, no enhancement in activity due to the presence of a hydroxy group
was found when the cytotoxicity of furanones 13a,b,d and 5-(1‘-hydroxyalkyl)-3-methylenedihydrofuran-2-ones 6a,b,d was compared. The anticancer activity of pyrrolidinones 16a−e and
3-alkylidenefuranones 18a−c was much weaker than that of furanones 13a−e.