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Beilstein J. Org. Chem. 2016, 12, 2793–2807, doi:10.3762/bjoc.12.278
Graphical Abstract
Figure 1: Some relevant MDM2-p53 interaction inhibitors.
Figure 2: Retrosynthetic route to spiro[isoindole-1,5-isoxazolidin]-3(2H)-ones 3.
Scheme 1: Synthesis of compounds 2.
Scheme 2: Synthesis of 6a–f by 1,3-dipolar cycloaddition.
Figure 3: Selected NOESY observed for compounds 6a and 7a.
Figure 4: ORTEP drawing of the X-ray crystal structure of 7a showing the model atomic numbering scheme (C10 a...
Scheme 3: Reaction pathway.
Figure 5: Three-dimensional plots of TSs of reaction of dipolarophiles (Z)-8 and (E)-8 with nitrone 4. The la...
Figure 6: Free energy profiles for the cycloaddition reaction of the two isomers Z (A) or E (B) of dipolaroph...
Figure 7: Compound 6e reduces cancer cell proliferation. Treatment of SH-SY5Y, HT-29 and HepG2 cells with 6e ...
Figure 8: Cytotoxic effect of 6e. The cytotoxic activity of 6e was assessed in terms of both LDH release (a) ...
Figure 9: 6e modulate the levels of p53 in SH-SY5Y cells. (a) The SH-SY5Y cells were treated for 24 h with th...
Figure 10: (A) Representative Western Blots and (B) semiquantitative analyses of p53, MDM2, p21 expression lev...
Figure 11: (A) Representative Western Blots and (B) densitometric analysis of caspase-3 and PARP cleavage in t...
Figure 12: Compounds 6a (green) and 6c (blue) docked into MDM2 structure (PDB-ID: 3LBL) superimposed on the ke...
Figure 13: A) Compounds 6e (green) docked into MDM2 structure (PDB-ID: 3LBL); His96 and p53 residue (yellow st...
Beilstein J. Org. Chem. 2015, 11, 328–334, doi:10.3762/bjoc.11.38
Figure 1: 2’-Oxa-3’-aza-modified nucleosides and 2’-oxa-3’-aza-modified nucleotides.
Figure 2: Triazolyl-2’-oxa-3’-aza-4’a-carbanucleosides.
Scheme 1: Synthesis of triazolyl isoxazolidinyl-nucleosides 13 and 14. Reagents and conditions: a) Tosyl chlo...
Figure 3: α–β Epimerization.