科研之友
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摘要
3-Aryl-2-diethoxyphosphoryl-4-nitrohexanoates 8, obtained by Michael addition of ethyl diethoxyphosphorylacetate 6 to 1-aryl-2-nitro-1-butenes 7, were utilized as convenient common intermediates in the synthesis of beta-aryl-gamma-ethyl-alpha-methylidene-gamma-lactones 17 and beta-aryl-gamma-ethyl-alpha-methylidene-gamma-lactams 21. Transformation of the nitro functionality in 8 into a hydroxyl or amino group and cyclization yielded lactones 16 or lactams 19, which were used in Horner-Wadsworth-Emmons olefination of formaldehyde to give target compounds in good yields. Cytotoxicity of these compounds was evaluated in vitro against mouse leukemia cell line L-1210 and two human leukemia cell lines, HL-60 and NALM-6. Two of the obtained compounds 17b,c with 4-bromophenyl and 4-methylphenyl substituents in the beta position proved to be very potent against all three cell lines with IC(50) values lower than 6 mu M.
- 出版日期2010
