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Synthesis and cytotoxicity of new thiazolo[4,5-b]pyridine-2(3H)-one derivatives based on α,β-unsaturated ketones and α-ketoacids

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Abstract

A series of thiazolo[4,5-b]pyridin-2(3H)-one derivatives were obtained via [3 + 3]-cyclization of 4-amino-5H-thiazol-2-one and α,β-unsaturated ketones or α-ketoacids. The structures of newly synthesized compounds were established by spectral data and a single-crystal X-ray diffraction analysis. Target compounds were screened for their anticancer activity according to US NCI protocols and moderate inhibitory activity against the tested cell line was confirmed. 5-Phenyl-7-(pyridin-3-yl)-3H-thiazolo[4,5-b]pyridin-2-one (3) and 2-oxo-7-thiophen-2-yl-2,3-dihydrothiazolo[4,5-b]pyridine-5-carboxylic acid (12) were screened for their cytotoxicity effects on HepG2 and Balb/c 3T3 cells which revealed promising results using MTT, NRU and TPC assays.

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Acknowledgements

The authors are grateful to Dr. V. L. Narayanan from Drug Synthesis and Chemistry Branch, National Cancer Institute, Bethesda, MD, USA, for in vitro evaluation of anticancer activity.

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Authors and Affiliations

  1. Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, Lviv, 79010, Ukraine

    Andrii Lozynskyi, Borys Zimenkovsky, Olexandra Roman & Roman Lesyk

  2. Department of Pharmacology and Toxicology, National Veterinary Research Institute, Partyzantow 57, 24-100, Pulawy, Poland

    Lidia Radko & Sylwia Stypula-Trebas

  3. Department of Organic Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, Poznan, 60-780, Poland

    Andrzej K. Gzella

Authors
  1. Andrii Lozynskyi
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  2. Borys Zimenkovsky
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  3. Lidia Radko
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  4. Sylwia Stypula-Trebas
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  7. Roman Lesyk
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Correspondence to Roman Lesyk.

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Lozynskyi, A., Zimenkovsky, B., Radko, L. et al. Synthesis and cytotoxicity of new thiazolo[4,5-b]pyridine-2(3H)-one derivatives based on α,β-unsaturated ketones and α-ketoacids. Chem. Pap. 72, 669–681 (2018). https://doi.org/10.1007/s11696-017-0318-1

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  • DOI: https://doi.org/10.1007/s11696-017-0318-1

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