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Synthesis and biological evaluation of some amino- and sulfanyl-3H-quinazolin-4-one derivatives as potential anticancer agents

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Abstract

A series of 6-substituted quinazolinone derivatives were prepared by the reaction of 6-bromoquinazolinones with aryl or alkyl amines and thiols, in the presence of a Pd(OAc)2/Xantphos system, under Buchwald–Hartwig-type reaction conditions. The 6-bromoquinazolinones were obtained in the three-components reaction of 5-bromoisatoic anhydride, triethyl orthoformate and an appropriate amine. Biological screening of the potential cytotoxicity of synthesized compounds on HT29 and HCT116 cell lines, as well as on the lymphocytes, showed that some derivatives of quinazolinone have significant anticancer activities. The detailed synthesis, spectroscopic data, and biological assays were reported.

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Acknowledgements

The authors gratefully acknowledge the use of the mass spectrometry services and facilities of the Center for Interdisciplinary Research of The John Paul II Catholic University of Lublin, Lublin, Poland, funded by POPW.01.03.00-06-003/09-00. The authors are grateful to the University of Lodz for a partial financial support.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12 Street, 91-403, Lodz, Poland

    Zbigniew Malinowski, Monika Nowak & Bartłomiej Borek

  2. Laboratory of Separation and Spectroscopic Method Applications, Center for Interdisciplinary Research, The John Paul II Catholic University of Lublin, Krasnicka Avenue 102, 20-718, Lublin, Poland

    Emilia Fornal

  3. Laboratory of Cytogenetics, Department of General Genetics, Molecular Biology, and Plant Biotechnology, Faculty of Biology and Environmental Protection, University of Lodz, Banacha 12/16 Street, 90-237, Lodz, Poland

    Renata Kontek & Gabriela Gajek

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  1. Zbigniew Malinowski
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  2. Emilia Fornal
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  3. Monika Nowak
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  4. Renata Kontek
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  5. Gabriela Gajek
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  6. Bartłomiej Borek
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Correspondence to Zbigniew Malinowski.

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Malinowski, Z., Fornal, E., Nowak, M. et al. Synthesis and biological evaluation of some amino- and sulfanyl-3H-quinazolin-4-one derivatives as potential anticancer agents. Monatsh Chem 146, 1723–1731 (2015). https://doi.org/10.1007/s00706-015-1508-6

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  • DOI: https://doi.org/10.1007/s00706-015-1508-6

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