Issue 4, 2013
From the journal:

Organic & Biomolecular Chemistry

Reactivity assessment of chalcones by a kinetic thiol assay†

Sabine Amslinger,‡*a   Nafisah Al-Rifai,‡a   Katrin Winter,a   Kilian Wörmann,a   Rebekka Scholz,a   Paul Baumeistera  and  Martin Wilda  

* Corresponding authors

a Institut für Organische Chemie, Universität Regensburg, Universitätsstraße 31, 93053 Regensburg, Germany
E-mail: sabine.amslinger@chemie.uni-regensburg.de
Fax: +49 941 943-4121
Tel: +49 941 943-4650

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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Article information

DOI
https://doi.org/10.1039/C2OB27163J
Article type
Communication
Submitted
07 Nov 2012
Accepted
21 Nov 2012
First published
21 Nov 2012

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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