Transient and intermediate carbocations in ruthenium tetroxide oxidation of saturated rings

Manuel Pedrón,
Laura Legnani,
Maria-Assunta Chiacchio,
Pierluigi Caramella,
Tomás Tejero and
Pedro Merino

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Published 11 Jul 2019

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1. Graphical Abstract
2. Scheme 1: Oxidation of alkanes with RuO₄.
  
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3. Scheme 2: Mechanisms for RuO₄ oxidation of alkanes.
  
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4. Scheme 3: Oxidation of saturated five-membered (hetero)cyclic compounds.
  
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5. Scheme 4: Rate-limiting step for the oxidation of cyclopentane (R1), tetrahydrofuran (R2) and tetrahydrothiop...
  
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6. Figure 1: Optimized (B3LYP-d3bj/Def2SVP/cpcm=MeCN) geometries of transition structures corresponding to the o...
  
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7. Figure 2: ELF analysis for the oxidation of cyclopentane (R1). Left: evolution of the electron population alo...
  
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8. Figure 3: ELF analysis for the oxidation of tetrahydrofuran (R2, A) and tetrahydrothiophene (R3, B). Left: ev...
  
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9. Figure 4: ELF assignment of electrons to the Ru environment. C(Ru) corresponds to a monosynaptic core basin a...
  
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10. Scheme 5: Rate-limiting step for the oxidation of N-methyl- and N-benzylpyrrolidines R4 and R5, respectively.
  
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11. Figure 5: Energy profile for the oxidation of R4 and R5. Relative energies, calculated at the B3LYP-d3bj/Def2...
  
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12. Figure 6: Optimized (B3LYP-d3bj/Def2SVP/cpcm=water) transition structures for the oxidation of R4 and R5.
  
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Beilstein J. Org. Chem. 2019, 15, 1552–1562, doi:10.3762/bjoc.15.158

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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

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Published 20 Dec 2016

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1. Graphical Abstract
2. Figure 1: Some relevant MDM2-p53 interaction inhibitors.
  
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3. Figure 2: Retrosynthetic route to spiro[isoindole-1,5-isoxazolidin]-3(2H)-ones 3.
  
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4. Scheme 1: Synthesis of compounds 2.
  
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5. Scheme 2: Synthesis of 6a–f by 1,3-dipolar cycloaddition.
  
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6. Figure 3: Selected NOESY observed for compounds 6a and 7a.
  
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7. Figure 4: ORTEP drawing of the X-ray crystal structure of 7a showing the model atomic numbering scheme (C10 a...
  
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8. Scheme 3: Reaction pathway.
  
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9. 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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10. Figure 6: Free energy profiles for the cycloaddition reaction of the two isomers Z (A) or E (B) of dipolaroph...
  
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11. Figure 7: Compound 6e reduces cancer cell proliferation. Treatment of SH-SY5Y, HT-29 and HepG2 cells with 6e ...
  
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12. Figure 8: Cytotoxic effect of 6e. The cytotoxic activity of 6e was assessed in terms of both LDH release (a) ...
  
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13. 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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14. Figure 10: (A) Representative Western Blots and (B) semiquantitative analyses of p53, MDM2, p21 expression lev...
  
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15. Figure 11: (A) Representative Western Blots and (B) densitometric analysis of caspase-3 and PARP cleavage in t...
  
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16. Figure 12: Compounds 6a (green) and 6c (blue) docked into MDM2 structure (PDB-ID: 3LBL) superimposed on the ke...
  
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17. Figure 13: A) Compounds 6e (green) docked into MDM2 structure (PDB-ID: 3LBL); His96 and p53 residue (yellow st...
  
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