Abstract

Synthesis of novel thiazolo [4,5-b] pyridines as potential biologically active substances

Author(s): Taras I. Chaban, Olena V. Klenina, Borys S. Zimenkovsky, Igor G. Chaban, Volodymyr V. Ogurtsov and Lesya S. Shelepeten

In an afford to develop novel anti-exudative and anti-oxidant agents, a series of thiazolo[4,5-b]pyridines were prepared by alcylation of the core scaffold in its N3 position and further ethoxy group nucleophilic replacement with hydrazine one. Hydrazine group functionalization included (5,7-Dimethyl-2-oxo-thiazolo[4,5-b]pyridine-3-yl)-acetic acid hydrazide treatment with thionyl-bis-glycolic acid leading to 2-(5,7-Dimethyl-2-oxo-thiazolo[4,5-b]pyridine-3- yl)-N-(4-oxo-2-thioxo-thiazolydine-3-yl)-acetamide generation and its interaction with carbon disulfide and KOH in equimolar amounts employed for 3-(5-mercapto-[1,3,4]oxodiazole-2-yl-methyl)-5,7-dimethyl-3H-thiazolo[4,5- b]pyridine-2-one potassium salt preparation. The presence of active methylene group in C5 position of 2-(5,7- Dimethyl-2-oxo-thiazolo[4,5-b]pyridine-3-yl)-N-(4-oxo-2-thioxo-thiazolydine-3-yl)-acetamide thiazolydine ring provided an entry for Knoevenagel condencation carrying out with the respective aryliden derivatives obtaining. More elaborate functionalization proceeding leaded to hydrazide group acylation with further hetarylsulfanyl moiety introducing. The anti-exudative effect of novel thiazolo[4,5-b]pyridine-2-one derivatives was evaluated in vivo employing the carrageenan-induced rat paw edema method. The antioxidant activity of the synthesized compounds was evaluated in vitro by the method of scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals.

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