Reactivity assessment of chalcones by a kinetic thiol assay

被引：45

作者：

Amslinger, Sabine ^{[1
]}

Al-Rifai, Nafisah ^{[1
]}

Winter, Katrin ^{[1
]}

Woermann, Kilian ^{[1
]}

Scholz, Rebekka ^{[1
]}

Baumeister, Paul ^{[1
]}

Wild, Martin ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 04期

关键词：

MICHAEL REACTION ACCEPTORS; INDUCERS; POTENCIES;

D O I：

10.1039/c2ob27163j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electrophilic nature of chalcones (1,3-diphenylprop-2-en-1-ones) and many other alpha,beta-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 alpha,beta-unsaturated carbonyl compounds k(2) values for curcumin and cinnamaldehyde were gained while cinnamic acids or esters gave no or very slow reactions.

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收藏

页码：549 / 554

页数：6

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