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Heterocycles 39. Synthesis, characterization and evaluation of the anti-inflammatory activity of thiazolo[3,2-b][1,2,4]triazole derivatives bearing pyridin-3/4-yl moiety

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Abstract

A series of pyridin-3/4-yl-thiazolo[3,2-b][1,2,4]triazole derivatives (5a–g, 6a–g) were synthesised by Hantzsch condensation of 5-pyridin-3/4-yl-1,2,4-triazole-3-thiol and diverse α-halocarbonyl compounds. Different reaction conditions (pH, temperature, solvent) were investigated for the efficient obtention of the target compounds. Under reflux and acidic conditions, the Hantzsch condensation was a one-step reaction. At room temperature and under basic conditions, it was possible to isolate the iminothioether intermediates 3/4a–g. These intermediates were cyclized in a subsequent step by treatment with concentrated sulphuric acid. The obtained compounds were evaluated for their anti-inflammatory activity. Three synthesised pyridyl-thiazolo[3,2-b][1,2,4]triazole derivatives (6c, 6d, 6f) were found to be good anti-inflammatory agents.

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Acknowledgements

This study was possible with the financial support of the European Social Fund, under the project POSDRU number 107/1.5/S/78702.

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Authors and Affiliations

  1. Department of Organic Chemistry, “Iuliu Haţieganu” University of Medicine and Pharmacy, 41 Victor Babeş street, Cluj-Napoca, Ro-400012, Romania

    Alexandra Toma, Denisa Leonte & Valentin Zaharia

  2. Department of Pharmacology, Physiology and Physiopathology, “Iuliu Haţieganu” University of Medicine and Pharmacy, 6A L. Pasteur street, Cluj-Napoca, Ro-400349, Romania

    Cristina Mogoşan

  3. Department of Pharmaceutical Technology and Biopharmaceutics, “Iuliu Haţieganu” University of Medicine and Pharmacy, 12 I. Creangă street, Cluj-Napoca, Ro-400010, Romania

    Laurian Vlase

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  1. Alexandra Toma
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  2. Cristina Mogoşan
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  3. Laurian Vlase
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  4. Denisa Leonte
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  5. Valentin Zaharia
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Correspondence to Denisa Leonte or Valentin Zaharia.

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Toma, A., Mogoşan, C., Vlase, L. et al. Heterocycles 39. Synthesis, characterization and evaluation of the anti-inflammatory activity of thiazolo[3,2-b][1,2,4]triazole derivatives bearing pyridin-3/4-yl moiety. Med Chem Res 26, 2602–2613 (2017). https://doi.org/10.1007/s00044-017-1959-x

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  • DOI: https://doi.org/10.1007/s00044-017-1959-x

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