SYNTHESIS AND BIOLOGICAL PROSPECTION OF NEW MICHAEL ACCEPTORS VIA MULTICOMPONENT REACTION

During the last years the advance in the understanding of the molecular bases of the carcinogenesis and the tumor progression has provided important tools for the monitoring of this disease. In particular, the p53 protein is one of the most important and most studied tumor suppressor genes and has been targeted
by most carcinogenic processes in humans and animals.1 Several classes of substances are capable of reactivating this protein, among them include the Michael acceptors.2
We have now found that 2,3-disubstituted-naphtho-[2,3-b]-furan-4,9-diones (4) can be directly obtained by the reactions of 2-hydroxy-1,4-naphthoquinones (1) with enamines, generated in situ, derived from ketones (2), under toluene reflux. In addition to the α-furan-naphthoquinones (4) of interest, we also obtained novel substances (5) formed by C-C bonds at the C-3 position of 1, which were converted into the isomers (6 and 7) by cyclization in sulfuric acid.