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

Solène Guihéneuf (1) , Ludovic Paquin (1) , François Carreaux (1) , Emilie Durieu (2) , Thierry Roisnel (1) , Laurent Meijer (3) , Jean-Pierre Bazureau (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 P3H - Phophorylation de protéines et Pathologies Humaines
3 ManRos Therapeutics

A practical approach for the preparation of ([Formula: see text]) 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 [Formula: see text]-substituted rhodanines 2(a-i). The ten synthetic products 3(a-j) have been synthesized with a [Formula: see text]-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 ([Formula: see text]) 5-ylidene rhodanine derivatives 3(a-j) were tested against eight protein kinases.

Mots clés: Rhodanine 5-Ylidene rhodanine Knoevenagel condensation Microwave condensation 2-Thioxo-imidazoline-4-one Kinase

Domaines: Autre

Solène Guihéneuf, Ludovic Paquin, François Carreaux, Emilie Durieu, Thierry Roisnel, et al.. New 5-ylidene rhodanine derivatives based on the dispacamide A model.. Molecular Diversity, 2014, 18 (2), pp.375-88. ⟨10.1007/s11030-014-9509-7⟩. ⟨hal-01017003⟩