Subject: synthesis; monocarbonyl analogs of curcumin; thiols; 2-(dimethylamino)ethanethiol; Michael addition
Year: 2023
Type: Article
Title: Development of a spectrophotometric method for assessment of the relative reactivity of monocarbonyl analogs of curcumin with 2-(dimethylamino)ethanethiol
Author: Zlatko Lozanovski, Jasmina Petreska Stanoeva,Jane Bogdanov
Abstract: 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 α,β-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 α,β-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 ≈ 6. The developed method is simple, and it can be extended to assess the reactivity of other MACs.
Publisher: Macedonial Journal of Cchemistry and Chemical Engineering
Relation: Macedonian Journal of Chemistry and Chemical Engineering
Identifier: oai:repository.ukim.mk:20.500.12188/27798
Identifier: http://hdl.handle.net/20.500.12188/27798Identifier: https://doi.org/10.20450/mjcce.2023.2638
