DOI: https://doi.org/10.24959/ophcj.19.174239

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

T. I. Chaban, Yu. E. Matiychuk, V. V. Ogurtsov, I. G. Chaban, V. S. Matiychuk

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; thiazolo[4,5-b]pyridines; antioxidant activity

References


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Chaban, T., Klenina, O., Harkov, S., Ogurtsov, V., Chaban, I., Nektegaev, I. (2017). Synthesis of some new N3 substituted 6-phenylazo-3Н-thiazolo[4,5-b]pyridin-2-ones as possible anti-inflammatory agents. Pharmacia, 64 (4), 16–30.

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Chaban, T. I., Ogurtsov, V. V., Matiychuk, V. S., Chaban, I. G., Demchuk, I. L., Nektegayev, I. A. (2019). Synthesis, anti-inflammatory and antioxidant activities of novel 3H-thiazolo[4, 5-b]pyridines. Acta Chimica Slovenica, 66 (1), 103–111. https://doi.org/10.17344/acsi.2018.4570

Chaban, T., Ogurtsov, V., Chaban, I., Myrko, I., Harkov, S., Lelyukh, M. (2019). Synthesis of some new 4-iminothiazolidine-2-ones as possible antioxidants agents. Pharmacia, 66 (1), 27–32. https://doi.org/10.3897/pharmacia.66.e35131

Blois, M. S. (1958). Antioxidant Determinations by the Use of a Stable Free Radical. Nature, 181, 1199–1200. https://doi.org/10.1038/1811199a0

Molyneux, P. J. (2004). The use of stable free radical diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity. Journal of Science and Technology, 26 (2), 211–219.


GOST Style Citations


1. Smirnova, N. G. Synthesis of condensed thiazoles / N. G. Smirnova, I. V. Zavarzin, M. M. Krayushkin // Chem. Heterocycl. Compd. – 2006. – Vol. 42, Issue 2. – P. 144–165. https://doi.org/10.1007/s10593-006-0064-8

 

2. Chaban, T. I. Methods of synthesis and properties of thiazolopyridines / T. I. Chaban // Журн. орган. та фармац. хімії. – 2015. – Т. 13, №1 (49). – С. 8–19. https://doi.org/10.24959/ophcj.15.811

 

3. Synthesis and antioxidant activity evaluation of novel 5,7-dimethyl-3H-thiazolo[4,5-b]pyridines / T. I. Chaban, V. V. Ogurtsov, I. G. Chaban et al. // Phosphorus, Sulfur, and Silicon and the Related Elements. – 2013. – Vol. 188, Issue 11. – P. 1611–1620. https://doi.org/10.1080/10426507.2013.777723


4. Синтез та вивчення антимікробної активності деяких тіазоло[4,5-b]піридинів / Т. І. Чабан, В. В. Огурцов, І. Г. Чабан, Й. Д. Комариця // Журн. орган. та фармац. хімії. – 2012. – Т. 10, № 2 (38). – С. 70–76.


5. Hegde, S. G. Synthesis and herbicidal activity of 5-(haloalkyl)-substituted thiazolo[4,5-b]pyridine-3(2H)-acetic acid derivatives / S. G. Hegde, M. D. Mahoney // J. Agric. Food Chem. – 1993. – Vol. 41. – P. 2131–2134. https://doi.org/10.1021/jf00035a058


6. Synthesis of some new N3 substituted 6-phenylazo-3Н-thiazolo[4,5-b]pyridin–2-ones as possible anti-inflammatory agents / T. Chaban, O. Klenina, S. Harkov et al. // Pharmacia. – 2017. – Vol. 64, Issue 4. – P. 16–30.


7. Al-Thebeiti, M. S. Synthesis of some new thiazolo[3,2-a]pyridines and related heterocyclic systems / M. S. Al-Thebeiti // Il Farmaco. – 2000. – Vol. 55, Issue 2. – P. 109–118. https://doi.org/10.1016/S0014-827X(99)00130-5


8. Synthesis and evaluation of antitumor activity of some thiazolo[4,5-b]pyridines / T. I. Chaban, R. R. Panchuk, O. V. Klenina et al. // Biopolym. Cell. – 2012. – Vol. 28, Issue 5. – P. 389–396. https://doi.org/10.7124/bc.000075


9. Walczyn´ski, K. Non-imidazole histamine H3 ligands. Part III. New 4-n-propylpiperazines as non-imidazole histamine H3-antagonists / K. Walczyn´ski, O. P. Zuiderveld, H. Timmerman // Eur. J. Med. Chem. – 2005. – Vol. 40, Issue 1. – P. 15–23. https://doi.org/10.1016/j.ejmech.2004.09.010


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