title: Reactivity assessment of chalcones by a kinetic thiol assay.
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 (k(2)) 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 k(2) values for curcumin and cinnamaldehyde were gained while cinnamic acids or esters gave no or very slow reactions.
authors.affiliation: Institut für Organische Chemie, Universität Regensburg, Universitätsstraße 31, 93053 Regensburg, Germany. sabine.amslinger@chemie.uni-regensburg.de
authors.forename: Sabine
authors.initials: S
authors.lastname: Amslinger
authors.forename: Nafisah
authors.initials: N
authors.lastname: Al-Rifai
authors.forename: Katrin
authors.initials: K
authors.lastname: Winter
authors.forename: Kilian
authors.initials: K
authors.lastname: Wörmann
authors.forename: Rebekka
authors.initials: R
authors.lastname: Scholz
authors.forename: Paul
authors.initials: P
authors.lastname: Baumeister
authors.forename: Martin
authors.initials: M
authors.lastname: Wild
mesh_terms: D047188:Chalcones / Q000737:chemistry*; D007700:Kinetics; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D047188:Chalcones; D013438:Sulfhydryl Compounds