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1 article(s) from Campisi, Agata

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

Salvatore V. Giofrè,
Santa Cirmi,
Raffaella Mancuso,
Francesco Nicolò,
Giuseppe Lanza,
Laura Legnani,
Agata Campisi,
Maria A. Chiacchio,
Michele Navarra,
Bartolo Gabriele and
Roberto Romeo

Beilstein J. Org. Chem. 2016, 12, 2793–2807, doi:10.3762/bjoc.12.278

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Graphical Abstract

Figure 1: Some relevant MDM2-p53 interaction inhibitors.

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Figure 2: Retrosynthetic route to spiro[isoindole-1,5-isoxazolidin]-3(2H)-ones 3.

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Scheme 1: Synthesis of compounds 2.

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Scheme 2: Synthesis of 6a–f by 1,3-dipolar cycloaddition.

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Figure 3: Selected NOESY observed for compounds 6a and 7a.

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Figure 4: ORTEP drawing of the X-ray crystal structure of 7a showing the model atomic numbering scheme (C10 a...

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Scheme 3: Reaction pathway.

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Figure 5: Three-dimensional plots of TSs of reaction of dipolarophiles (Z)-8 and (E)-8 with nitrone 4. The la...

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Figure 6: Free energy profiles for the cycloaddition reaction of the two isomers Z (A) or E (B) of dipolaroph...

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Figure 7: Compound 6e reduces cancer cell proliferation. Treatment of SH-SY5Y, HT-29 and HepG2 cells with 6e ...

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Figure 8: Cytotoxic effect of 6e. The cytotoxic activity of 6e was assessed in terms of both LDH release (a) ...

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Figure 9: 6e modulate the levels of p53 in SH-SY5Y cells. (a) The SH-SY5Y cells were treated for 24 h with th...

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Figure 10: (A) Representative Western Blots and (B) semiquantitative analyses of p53, MDM2, p21 expression lev...

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Figure 11: (A) Representative Western Blots and (B) densitometric analysis of caspase-3 and PARP cleavage in t...

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Figure 12: Compounds 6a (green) and 6c (blue) docked into MDM2 structure (PDB-ID: 3LBL) superimposed on the ke...

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Figure 13: A) Compounds 6e (green) docked into MDM2 structure (PDB-ID: 3LBL); His96 and p53 residue (yellow st...

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Published 20 Dec 2016

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