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Issue 4, 2010
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A convenient synthesis and cytotoxic evaluation of β-aryl-α-methylidene-γ-lactones and β-aryl-α-methylidene-γ-lactams

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Abstract

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.

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

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Article information


Submitted
08 Dec 2009
Accepted
15 Jan 2010
First published
24 Feb 2010

New J. Chem., 2010,34, 750-761
Article type
Paper

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

A. Albrecht, Ł. Albrecht, M. Różalski, U. Krajewska, A. Janecka, K. Studzian and T. Janecki, New J. Chem., 2010, 34, 750
DOI: 10.1039/B9NJ00740G

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