A series of spiro[isoindole-1,5-isoxazolidin]-3(2H)-ones has been synthesized by 1,3-dipolar cycloaddition of N-benzylnitrone with isoindolin-3-methylene-1-ones. The regio- and stereoselectivity of the process have been rationalized by computational methods. The obtained compounds show cytotoxic properties and antiproliferative activity in the range of 9-22 μM. Biological tests suggest that the antitumor activity could be linked to the inhibition of the protein-protein p53-MDM2 interaction. Docking measurements support the biological data.
Giofrè, S., Cirmi, S., Mancuso, R., Nicolò, F., Lanza, G., Legnani, L., et al. (2016). Synthesis of spiro[isoindole-1,5′-isoxazolidin]-3(2H)-ones as potential inhibitors of the MDM2-p53 interaction. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 12, 2793-2807 [10.3762/bjoc.12.278].
Synthesis of spiro[isoindole-1,5′-isoxazolidin]-3(2H)-ones as potential inhibitors of the MDM2-p53 interaction
LEGNANI, LAURA;
2016
Abstract
A series of spiro[isoindole-1,5-isoxazolidin]-3(2H)-ones has been synthesized by 1,3-dipolar cycloaddition of N-benzylnitrone with isoindolin-3-methylene-1-ones. The regio- and stereoselectivity of the process have been rationalized by computational methods. The obtained compounds show cytotoxic properties and antiproliferative activity in the range of 9-22 μM. Biological tests suggest that the antitumor activity could be linked to the inhibition of the protein-protein p53-MDM2 interaction. Docking measurements support the biological data.
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