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Heterocycles 44. Synthesis, characterization and anticancer activity of new thiazole ortho-hydroxychalcones

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Abstract

A novel series of substituted thiazole ortho-hydroxychalcones was synthesized to be physico-chemically characterized and evaluated for the anticancer activity. The chalcones were synthesized with 28–68% yields, via Claisen–Schmidt condensation in an ethanolic solution. All the synthesized compounds were purified and characterized by MS, 1H NMR, 13C NMR, IR, and melting points. The cytotoxicity of thiazole ortho-hydroxychalcones 3a–3o as well as doxorubicin was determined in a panel of 9 cancer cell lines including sensitive and drug resistant phenotypes. Compounds 3a, 3b, 3c, 3j, as well as doxorubicin displayed cytotoxic effects in all the 9 tested cancer cell lines with IC50 values below 75 µM. The best samples showed IC50 values below 10 µM against 5/9 cancer cell lines for 3a, 3h, and 3o, against 7/9 cancer cell lines for 3c and 3f, and against 8/9 cancer cell lines for 3j. Hypersensitivity of all resistant cells towards 3b, 3g, 3j, 3m, and 3o was also obtained, suggesting that these compounds are appropriate molecules that could be used to combat drug resistance of cancer cells.

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Acknowledgements

The work described here is published under the research contract financed by “Iuliu Haţieganu” University of Medicine and Pharmacy Cluj-Napoca, Romania, by internal grant no. 7690/27 from 15.04.2016. VK is very grateful to the Alexander von Humboldt Foundation for the funding through the Linkage program (2015–2018); ATM is thankful to Alexander von Humboldt Foundation for an 18 months fellowship in Prof. Dr. Thomas Efferth’s laboratory in Mainz, Germany through the “Georg Foster Research Fellowship for Experienced Researcher program”.

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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, 400012, Romania

    Fana-Maria Coman, Denisa Leonte & Valentin Zaharia

  2. Department of Pharmaceutical Biology, Institute of Pharmacy and Biochemistry, Johannes Gutenberg University, Stawdenger Weg 5, Mainz, 55128, Germany

    Armelle T. Mbaveng, Victor Kuete & Thomas Efferth

  3. Department of Biochemistry, Faculty of Science, University of Dschang, Dschang, Cameroon

    Armelle T. Mbaveng & Victor Kuete

  4. Faculty of Chemistry and Chemical Engineering, Biocatalysis and Biotransformation Research Group, “Babeş-Bolyai” University, 11 Arany János Street, Cluj-Napoca, 400028, Romania

    László Csaba Bencze

  5. Department of Pharmaceutical Technology and Biopharmaceutics, “Iuliu Haţieganu” University of Medicine and Pharmacy, 41 Victor Babeş Street, Cluj-Napoca, 400012, Romania

    Laurian Vlase

  6. Department of Analytical Chemistry and Drug Analysis, University of Medicine and Pharmacy Tîrgu Mureş, 38 Gheorghe Marinescu Street, Târgu Mureş, 540139, Romania

    Silvia Imre

Authors
  1. Fana-Maria Coman
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  2. Armelle T. Mbaveng
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  3. Denisa Leonte
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  4. László Csaba Bencze
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  5. Laurian Vlase
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  6. Silvia Imre
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  7. Victor Kuete
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  8. Thomas Efferth
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  9. Valentin Zaharia
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Corresponding authors

Correspondence to Thomas Efferth or Valentin Zaharia.

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Coman, FM., Mbaveng, A.T., Leonte, D. et al. Heterocycles 44. Synthesis, characterization and anticancer activity of new thiazole ortho-hydroxychalcones. Med Chem Res 27, 1396–1407 (2018). https://doi.org/10.1007/s00044-018-2156-2

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  • DOI: https://doi.org/10.1007/s00044-018-2156-2

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