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Synthesis of spiro[isoindole-1,5'-isoxazolidin]-3(2H)-ones as potential inhibitors of the MDM2-p53 interaction.


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 ?M. 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.

SUBMITTER: Giofre SV 

PROVIDER: S-EPMC5238597 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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Synthesis of spiro[isoindole-1,5'-isoxazolidin]-3(2<i>H</i>)-ones as potential inhibitors of the MDM2-p53 interaction.

Giofrè Salvatore V SV   Cirmi Santa S   Mancuso Raffaella R   Nicolò Francesco F   Lanza Giuseppe G   Legnani Laura L   Campisi Agata A   Chiacchio Maria A MA   Navarra Michele M   Gabriele Bartolo B   Romeo Roberto R  

Beilstein journal of organic chemistry 20161220


A series of spiro[isoindole-1,5-isoxazolidin]-3(2<i>H</i>)-ones has been synthesized by 1,3-dipolar cycloaddition of <i>N</i>-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 int  ...[more]

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