Psoralens are natural products present in several plant families that are extremely toxic
to a wide variety of prokaryotic and eukaryotic organisms. They are potentially active in
diseases such as vitiligo, psoriasis, and several types of cancer. Following our interest
on this type of compounds 1 four new psoralen analogues were prepared, 1a-1c and 1e.
To synthesize 1a (R = H) the method of Harayama and Ishii was used where the
cinnamate was obtained by the Wittig reaction followed by ring closure. Condensation
of 1-formyl-2-hydroxycarbazole with diethyl malonate gave 1b which by basic
hydrolysis yielded compound 1c. Compound 1d was prepared before.2 Condensation of
the 2-hydroxycarbazole with ethyl acetoacetate gave 1e. The products were
characterized by elemental analysis, 1H and 13C NMR. Moreover, the anti-proliferative
effect of compounds 1a-1e on human cancer cell lines (MDA-MB 231, HeLa and TCCSUP)
was evaluated. Results suggest that these psoralen analogues possess a potent
cytotoxic effect against the cell lines studied. Computational and molecular docking
studies are being carried out.Fundação para a Ciência e a Tecnologia (FCT)(PEst-C/QUI/UI0686/2011), FEDER-COMPET
