Prospective study directed to the synthesis of unsymmetrical linked bis-5-arylidene rhodanine derivatives via “one-pot two steps” reactions under microwave irradiation with their antitumor activity

Wacothon Karime Coulibaly (1) , Ludovic Paquin (1) , Anoubilé Bénie (2) , Yves-Alain Békro (2) , Rémy Le Guével (3) , Myriam Ravache (3) , Anne Corlu (3) , Jean Pierre Bazureau (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LCBOSN - Laboratoire de Chimie Bioorganique et des Substances Naturelles
3 GFAS - Génétique fonctionnelle, agronomie et santé [IFR 140]

We here report on the synthesis of new unsymmetrical linked bis-5-arylidene rhodanine derivatives with stereocontrolled Z-configuration. The 6 steps synthesis was achieved and the key steps are the construction of the two 5-arylidene rhodanine moieties using an “one-pot two-steps” method under microwave dielectric heating in a closed reactor. The intermediates 6, 7 and desired unsymmetrical compounds 9 have been also evaluated for their in vitro inhibition of cell proliferation (Huh7 D12, Caco2, MDA-MB 231, HCT116, and NCI-H727 tumoral cell lines). Two of all compounds have shown potent activity against Huh7 D12, Caco2, and MDA-MB 231.

Keywords: Microwave Knoevenagel condensation Rhodanine 5-Arylidene-2-thioxo-1; 3-thiazolidine-4-one Unsymmetrical bis-rhodanine Tumoral lines

Domains: Chemical Sciences

Wacothon Karime Coulibaly, Ludovic Paquin, Anoubilé Bénie, Yves-Alain Békro, Rémy Le Guével, et al.. Prospective study directed to the synthesis of unsymmetrical linked bis-5-arylidene rhodanine derivatives via “one-pot two steps” reactions under microwave irradiation with their antitumor activity. Medicinal Chemistry Research, 2015, 24 (4), pp.1653-1661. ⟨10.1007/s00044-014-1186-7⟩. ⟨hal-01114518⟩