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Microwave-accelerated multicomponent synthesis and X-ray characterization of novel benzothiadiazinone dioxide derivatives, analogues of Monastrol

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Abstract

We demonstrate here a rapid and comfortable synthetic sequence to benzothiadiazinone dioxide (six-membered cyclic sulfamide) derivatives, analogues of Monastrol, which is known to be a specific mitotic kinesin Eg5 inhibitor. Fourteen novel compounds (1d–14d) were synthesized through three component Biginelli reaction, by condensation of aromatic aldehyde, sulfamide, and cyclohexane-1,3-dione. A wide range of substrates is compatible in this reaction, producing excellent yields (82–92%) in short time (5–10 min). The reaction is performed under solvent-free, catalysed by H2SO4/CH3COOH (1/9) using microwave irradiation. The structure of the obtained substances was confirmed by 1H, 13C, HMBC, HSQC NMR spectroscopy, IR spectroscopy, and mass spectrometry, as well as elemental analysis. A single crystal of the (4-phenyl-4,6,7,8-tetrahydro-1H benzo[c][1,2,6]thiadiazin-5(3H)-one 2,2-dioxide has been obtained after recrystallization in ethanol/acetone (9/1) and selected for X-ray study.

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Acknowledgements

This work was supported financially by The General Directorate for Scientific Research and Technological Development (DG-RSDT), Algerian Ministry of Scientific Research, Applied Organic Chemistry Laboratory (FNR 2000).

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Authors and Affiliations

  1. Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Department of Chemistry, Sciences Faculty, Badji-Mokhtar - Annaba University, Box 12, 23000, Annaba, Algeria

    Abdeslem Bouzina, Malika Berredjem, Billel Belhani & Mohamed Aissaoui

  2. Département Sciences de la Matière, Université Oum El Bouaghi, 04000, Oum El Bouaghi, Algeria

    Sofiane Bouacida

  3. Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, Université Constantine 1, 5000, Constantine, Algeria

    Sofiane Bouacida

  4. SFR Santé Lyon-Est CNRS UMS3453-INSERM US7, EA 4446 Bioactive Molecules and Medicinal Chemistry, Faculté de Pharmacie-ISPB, Université Lyon 1, Université de Lyon, 69373, Lyon Cedex 8, France

    Christelle Marminon, Marc Le Borgne & Zouhair Bouaziz

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  1. Abdeslem Bouzina
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Correspondence to Malika Berredjem.

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Bouzina, A., Berredjem, M., Belhani, B. et al. Microwave-accelerated multicomponent synthesis and X-ray characterization of novel benzothiadiazinone dioxide derivatives, analogues of Monastrol. Res Chem Intermed 47, 1359–1376 (2021). https://doi.org/10.1007/s11164-020-04378-3

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