DEVELOPMENT OF A SPECTROPHOTOMETRIC METHOD FOR ASSESSMENT OF THE RELATIVE REACTIVITY OF MONOCARBONYL ANALOGS OF CURCUMIN WITH 2-(DIMETHYLAMINO)ETHANETHIOL

Zlatko Lozanovski, Z.L. and Jasmina Petreska Stanoeva, J.P.S and Jane Bogdanov, J.B. DEVELOPMENT OF A SPECTROPHOTOMETRIC METHOD FOR ASSESSMENT OF THE RELATIVE REACTIVITY OF MONOCARBONYL ANALOGS OF CURCUMIN WITH 2-(DIMETHYLAMINO)ETHANETHIOL. Macedonian Journal of Chemistry and Chemical Engineering.

	Text 1168 Download (3kB)
	Text 1168 Download (3kB)

Official URL: https://mjcce.org.mk/index.php/MJCCE/index

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 pro-cesses 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 correspond-ing 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.Keywords:synthesis; monocarbonyl analogs of curcumin; thiols; 2-(dimethylamino)ethanethiol; Michael addition

Item Type:	Article
Subjects:	Scientific Fields (Frascati) > Natural sciences > Chemical sciences
Divisions:	Higher Medical School
Depositing User:	PhD Zlatko Lozanovski
Date Deposited:	27 Feb 2025 14:53
Last Modified:	27 Feb 2025 14:53
URI:	https://eprints.uklo.edu.mk/id/eprint/10786

Actions (login required)

View Item