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Comparison between Conventional and Nonconventional Methods for the Synthesis of Some 2-Oxazolidinone Derivatives and Preliminary Investigation of Their Inhibitory Activity Against Certain Protein Kinases

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Abstract

A series of propargyl and allyl carbamates were prepared directly from propargyl and allyl alcohols and phenyl or cyclohexyl isocyanate or indirectly by generating the isocyanates in situ from the corresponding Cbz-protected amines. The obtained carbamates underwent intramolecular nucleophilic cyclization in presence of cesium hydroxide monohydrate as a base catalyst under conventional and ultrasonic irradiation conditions to give the corresponding substituted 4-(benzylidene)methylidene-2-oxazolidinones in good to excellent yields. The use of ultrasonic irradiation provided remarkably improved yield of the cyclization products and significant shortening of the reaction time. In some cases the reaction was highly stereoselective, and (Z)-4-benzylideneoxazolidinones were formed as a single stereoisomer. A series of biological tests were performed to evaluate the inhibitory potential of all synthesized compounds against some protein kinases.

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Acknowledgements

The authors are grateful to Prof. Dr. Ramesh Ramapanicker (Indian Institute of Technology, Kanpur, India) for providing laboratory facilities.

Funding

This study was performed under financial support by the Ministry of Higher Education and Scientific Research of Algeria (grant no. 571/PNE/Doctorant/India/2016-2017).

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Authors and Affiliations

  1. Laboratoire de Synthèse Organique Appliquée, Département de Chimie, Faculté des sciences exactes et appliquées, Université Oran 1 Ahmed Ben Bella, Oran, Algeria

    S. Ziane, M. M. Mazari, A. M. Safer & A. Sad El Hachemi Amar

  2. Station biologique de Roscoff, Roscoff, France

    S. Ruchaud, B. Baratte & S. Bach

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  1. S. Ziane
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  2. M. M. Mazari
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  3. A. M. Safer
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  4. A. Sad El Hachemi Amar
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  5. S. Ruchaud
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  6. B. Baratte
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  7. S. Bach
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Correspondence to S. Ziane.

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No conflict of interests is declared by the authors.

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Ziane, S., Mazari, M.M., Safer, A.M. et al. Comparison between Conventional and Nonconventional Methods for the Synthesis of Some 2-Oxazolidinone Derivatives and Preliminary Investigation of Their Inhibitory Activity Against Certain Protein Kinases. Russ J Org Chem 55, 1061–1069 (2019). https://doi.org/10.1134/S1070428019070248

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  • DOI: https://doi.org/10.1134/S1070428019070248

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