期刊
MACEDONIAN JOURNAL OF CHEMISTRY AND CHEMICAL ENGINEERING
卷 42, 期 1, 页码 13-24出版社
SOC CHEMISTS TECHNOLOGISTS MADECONIA
DOI: 10.20450/mjcce.2023.2638
关键词
synthesis; monocarbonyl analogs of curcumin; thiols; 2-(dimethylamino)ethanethiol; Michael addition
To enhance the bioavailability of curcumin, researchers have developed monocarbonyl analogs of curcumin (MACs) with an electrophilic α,β-unsaturated carbonyl group and evaluated their biological activity. The MACs can react with thiol compounds to regulate important biological processes. In this study, MACs were synthesized through Claisen-Schmidt condensation reaction and their reactivity with 2-(dimethylamino)ethanethiol was assessed using a spectrophotometric method based on UV-Vis spectra.
In order to improve the bioavailability of curcumin, studies have been undertaken to prepare the so-called monocarbonyl analogs of curcumin (MACs) and assess their biological activity. These analogs contain an electrophilic & alpha;,& beta;-unsaturated carbonyl moiety (Michael acceptor). Several key biological processes are connected/controlled with thiol alkylation (glutathione, cysteine, cysteine peptide residues). The most likely reaction is the Michael addition between the & alpha;,& beta;-unsaturated acceptor and a corresponding thiol. 2,6-Bisarylidenecyclohexanone and 3,5-bisarylidenepiperidin-4-one scaffolds offer convenient tunability of electrophilicity and redox properties of the Michael acceptor by the introduction of various substituents. In this study, several MACs were prepared by Claisen-Schmidt condensation reaction, and their reactivity with 2-(dimethylamino)ethanethiol was evaluated. For this purpose, based on the UV-Vis spectra of the analogs and thiol(s), a proper method for spectrophotometric evaluation of their reactivity with 2-(dimethylamino)ethanethiol was optimized. The relative reactivity of the analogs was 7 > 2 > 5 > 4 > 1 & AP; 6. The developed method is simple, and it can be extended to assess the reactivity of other MACs.
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