Abstract
The metal-catalyzed dimerization of 2,3-diferrocenyl 1a and 2,3-diaryl-cyclopropenones 1b-c was used to synthesize tetrasubstituted spirolactones 2a-c, 3b-c and 4b-c. The dimerization of 1a-c was carried out with different metals as the catalyst with the following descending reactivity Au°>Ag°>Cu°>Zn°>Cd°>Bi°, where the Au led to a 74 %, 26 % & 48 % conversion for 2a-c respectively. All compounds were characterized by 1H and 13C NMR spectroscopy, IR, elemental analysis and a single crystal X-ray diffraction analysis of 2a. The electrochemical properties of compounds 2a-c and 3b-c were studied by cyclic voltammetry. Electron transfers were observed for tetraferrocenylspirolactone 2a and two electron transfers for compounds 2b and 3b. Cell viability studies are carried out in six different lines of human cancer cell (U-251, PC-3, K-562, HCT-15, MCF-7, SKLU-1) for compounds 2a-c y 3b-c, where it was found that 1,2,6,7-tetraphenyl-4-oxaspiro [2.4] hepta-1,6-dien-5-one 2b has the most promising cytotoxic properties. The morphology of the lines HCT-15, MCF-7, PC-3 was studied, and it is plausible that the mechanism of action of cell death is apoptosis, due to cellular morphological changes.
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