Synthesis of unexpected novel bis-coumarin derivatives via three component reactions of 4-hydroxycoumarin, aldehydes and cyclic secondary amines. Conformation in the solid state and pharmacological evaluation

Abstract

Abstract A series of unexpected bis-coumarins have been synthesized by multicomponent reactions of 4-hydroxycoumarin, aldehydes, and cyclic secondary amines in ethanol at room temperature. The chemical structures of new compounds were identified by 1H, 13C NMR, and mass spectrometry. Furthermore, the molecular structure of the solid-state adduct of 3,3′-[(4-methoxyphenyl)-methylene]bis(4-hydroxy-2H-chromen-2-one) with morpholine (1:1) has been confirmed by single-crystal X-ray diffraction. The cytotoxicity of the new coumarin derivatives against MCF7 breast cancer cells was evaluated. A docking study of the new products was carried out to assess the molecular affinity between the tested compound and Topoisomerase IIa.