Microwave Assisted Organic Synthesis (MAOS) of New Dispacamide A Derivatives Bearing a Thiazolinone Platform, Biological Assays on Inhibition of Protein Kinases and Cell Effects
Solene Guiheneuf, Ludovic Paquin, Francois Carreaux, Emilie Durieu, Helene Benedettid, Remy Le Guevel, Anne Corlu, Laurent Meijer and Jean-Pierre Bazureau
Affiliation: Universite de de Rennes 1, Institut des Sciences Chimiques de Rennes ISCR UMR CNRS 6226, groupe Ingenierie Chimique et Molecules pour le Vivant (ICMV), Bat. 10 A, Campus de Beaulieu, CS 74205, 263 Avenue du General Leclerc, 35042 Rennes Cedex, France.
A series of (5Z)-5-ylidene-thiazolidine-4-one derivatives bearing the N-(4,5-dihalogenopyrrol-2-yl)carbamoyl
fragment of Dispacamide A was prepared through a newly developed approach using a solution phase protocol assisted by
microwave irradiation. These new compounds were synthesized in good yields (10-98%) by sulphur/nitrogen displacement
or eventually by Knoevenagel condensation in the presence of a base (AcONa) in AcOH solution. The ten synthetic
products have been obtained with a Z-geometry about their exocyclic double bond. All these compounds have been evaluated
against eight protein kinases and human cell lines.
Keywords: Cell line, Dispacamide A, 2-imino-thiazolidine-4-one, inhibition, Knoevenagel reaction, microwave, solution phase,
thiazolidine-4-one, sulphur/nitrogen displacement, protein kinase.
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