Artigo Revisado por pares

A convenient synthesis and cytotoxic evaluation of β-aryl-α-methylidene-γ-lactones and β-aryl-α-methylidene-γ-lactams

2010; Royal Society of Chemistry; Volume: 34; Issue: 4 Linguagem: Inglês

10.1039/b9nj00740g

ISSN

1369-9261

Autores

Anna Albrecht, Łukasz Albrecht, Marek Różalski, Urszula Krajewska, Anna Janecka, Kazimierz Studzian, Tomasz Janecki,

Tópico(s)

Organophosphorus compounds synthesis

Resumo

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 β-aryl-γ-ethyl-α-methylidene-γ-lactones 17 and β-aryl-γ-ethyl-α-methylidene-γ-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 β position proved to be very potent against all three cell lines with IC50 values lower than 6 μM.

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