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Issue 4, 2013
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Reactivity assessment of chalcones by a kinetic thiol assay

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Abstract

The electrophilic nature of chalcones (1,3-diphenylprop-2-en-1-ones) and many other α,β-unsaturated carbonyl compounds is crucial for their biological activity, which is often based on thiol-mediated regulation processes. To better predict their biological activity a simple screening assay for the assessment of the second-order rate constants (k2) in thia-Michael additions was developed. Hence, a clear structure–activity relationship of 16 differentially decorated hydroxy-alkoxychalcones upon addition of cysteamine could be established. Moreover, amongst other naturally occurring α,β-unsaturated carbonyl compounds k2 values for curcumin and cinnamaldehyde were gained while cinnamic acids or esters gave no or very slow reactions.

Graphical abstract: Reactivity assessment of chalcones by a kinetic thiol assay

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Publication details

The article was received on 07 Nov 2012, accepted on 21 Nov 2012 and first published on 21 Nov 2012


Article type: Communication
DOI: 10.1039/C2OB27163J
Org. Biomol. Chem., 2013,11, 549-554

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    Reactivity assessment of chalcones by a kinetic thiol assay

    S. Amslinger, N. Al-Rifai, K. Winter, K. Wörmann, R. Scholz, P. Baumeister and M. Wild, Org. Biomol. Chem., 2013, 11, 549
    DOI: 10.1039/C2OB27163J

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