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New 5-ylidene rhodanine derivatives based on the dispacamide A model

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Abstract

A practical approach for the preparation of (\(5Z\)) 5-ylidene rhodanine derivatives bearing the (4,5-dihalogeno-pyrrol-2-yl)carbamoyl fragment of dispacamide A is reported. The new compounds were obtained in good yields (19–88 %) by Knoevenagel condensation according to a solution-phase microwave dielectric heating protocol in the presence of organic bases (piperidine, TEA, and AcONa) from a set of \(N\)-substituted rhodanines 2(a–i). The ten synthetic products 3(a–j) have been synthesized with a \(Z\)-geometry about their exocyclic double bond and the structure of one of these compounds (3) was confirmed by a single X-ray diffraction analysis. The new (\(5Z\)) 5-ylidene rhodanine derivatives 3(a–j) were tested against eight protein kinases.

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Acknowledgments

One of us (S.G.) wishes to thank the “Ministère de la Recherche et de l’Enseignement Supérieur” for research fellowships. Financial support of this program carried out under the French National Cancer Institute “Cancéropôle Grand Ouest” by contracts PRIR 04-8390 and ACI 04-2254, is gratefully acknowledged.

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Authors and Affiliations

  1. Université de Rennes 1 Institut des Sciences Chimiques de Rennes ISCR UMR CNRS 6226, groupe Ingénierie Chimique et Molécules pour le Vivant (ICMV), Bât. 10 A, Campus de Beaulieu, CS 74205, 263 Avenue du Général Leclerc, 35042,  Rennes Cedex, France

    Solene Guiheneuf, Ludovic Paquin, François Carreaux & Jean-Pierre Bazureau

  2. Station Biologique CNRS, Protein Phosphorylation & Human Disease, USR 3151, Place Georges Teissier, CS 90074, 29688,  Roscoff Cedex, France

    Emilie Durieu

  3. Université de Rennes 1, Institut des Sciences Chimiques de Rennes ISCR UMR CNRS 6226, Centre de Diffractométrie X (cdifx), Bât. 10 B, Campus de Beaulieu, CS 74205, 263 Avenue du Général Leclerc, 35042,  Rennes Cedex, France

    Thierry Roisnel

  4. ManRos Therapeutics (from Sea to Pharmacy), Hôtel de Recherche, Centre de Perharidy, 29680,  Roscoff, France

    Laurent Meijer

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  1. Solene Guiheneuf
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  2. Ludovic Paquin
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Correspondence to Jean-Pierre Bazureau.

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Guiheneuf, S., Paquin, L., Carreaux, F. et al. New 5-ylidene rhodanine derivatives based on the dispacamide A model. Mol Divers 18, 375–388 (2014). https://doi.org/10.1007/s11030-014-9509-7

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