Synthesis of some new N3 substituted 5-hydroxy-7-methyl-3H-thiazolo[4,5-b]pyridin-2-ones as potential biologically active compounds

Abstract

Condensed bicyclic systems with thiazolidine core being annulated to pyridine one occupy prominent place in medicinal chemistry because of their broad spectrum of pharmacological activities. So, the synthesis of new N3 substitutes thiazolo[4,5-b]pyridines is relevant with prospect of studying biological activity of the obtained substances. Aim. Expanding the synthetic potential of thiazolo[4,5-b]pyridines, the study of reactivity and synthesis of new N3 substituted 5-hydroxy-7-methyl-3H-thiazolo[4,5-b]pyridin-2-one derivatives. Materials and methods. Methods of organic synthesis; Physical and physical-chemical methods of analysis of organic compounds (1H NMR spectroscopy, elemental analysis). Results. Changes were made in the main heterocycle at position N3 in order to obtain new thiazolo[4,5-b]pyridines. It turned out that the combination of the reaction of cyanethylation and acid hydrolysis is an effective method of the synthesis of inaccessible 3-(5-hydroxy-7-methyl-2-oxo-thiazolo[4,5-b]pyridin-3-yl)-propionic acid. It helped to obtain a group of amides of this heterocyclic acid as perspective biologically active compounds. The structure of all synthesized compounds was confirmed by the 1H NMR spectroscopy and the data of elemental analysis. Conclusions. As a result of the structural modification of 5-hydroxy-7-methyl-3H-thiazolo[4,5-b]pyridine-2-one at position N3, a series of new thiazolo[4,5-b]pyridine-2-ones were synthesized. Pharmacological screening of the obtained thiazolo[4,5-b]pyridines was carried out. We continue to research different activities and chemical transformation of these substances with the prospect of studying biological activities.

Keywords

• thiazolo[4
• 5-b]pyridines
• cyanethylation
• hydrolysis
• acylation