Synthesis and antioxidant properties of novel thiazolo[4,5-b]pyridine-2-ones

Abstract

Aim. To expand the synthetic potential of thiazolo[4,5-b]pyridines, study the reactivity and perform the pharmacological screening of the antioxidant activity of the novel compounds synthesized. Results and discussion. A series of novel 3-aryl-5-hydroxy-7-methyl-3H-thiazolo[4,5-b]pyridine-2-ones were obtained as a result of the interaction of 3-aryl-4-iminothiazolidine-2-ones with ethyl acetoacetate. At this stage the resulting 3-phenyl-5-hydroxy-7-methyl-3H-thiazolo[4,5-b]pyridin-2-one was modified in position 5 in the acylation reaction. For all compounds synthesized the primary pharmacological screening of the antioxidant activity was performed; the results showed the potential for the search of antioxidant agents among thiazolo[4,5-b]pyridine-2-ones. Experimental part. By the reactions of [3+3]-cyclocondensation and acylation 12 novel thiazolo[4,5-b]pyridine-2-ones were obtained. The structure of all compounds synthesized was confirmed by the method of 1H NMR-spectroscopy and the data of elemental analysis. The antioxidant activity of the compounds synthesized was investigated in vitro by the method of scavenging effect on 2,2-diphenyl-1-picrylhydrazyl radical. Conclusions. 12 novel thiazolo[4,5-b]pyridines have been synthesized, their antioxidant properties have been investigated, and prospectivity for the search of novel antioxidant agents among thiazolo[4,5-b]pyridines has been shown.

Keywords

• organic synthesis
• thiazolopyridines
• antioxidant activity