An efficient one-pot three-component synthesis of 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-arylacrylonitriles and their cytotoxic activity evaluation with molecular docking

A facile, convenient and one-pot three-component method has been outlined for the synthesis of title compounds by treating equimolar amounts of 3-(2-bromoacetyl)-2H-chromen-2-one (2) with 2-cyanothioacetamide (3) and various aryl/heteryl aldehydes (5 or 7) independently. The effect of solvent and catalyst on this one-pot reaction has been studied and the use of L-proline in ethanol was found to be effective to achieve the target compounds (6 & 8) in fair yields. These synthesized compounds were further assessed for the anti-hepatoma activity, and their action mechanism was also investigated by using molecular docking studies. All the compounds 6(a-h) & 8(a-f) manifested excellent potency for anti-hepatoma activity. It should be noted that, compounds 6e, 6f have exhibited almost equipotent activity with reference to standard drug Nexavar. (C) 2018 Production and hosting by Elsevier B.V. on behalf of King Saud University.