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2 article(s) from Périgaud, Christian

Revaluation of biomass-derived furfuryl alcohol derivatives for the synthesis of carbocyclic nucleoside phosphonate analogues

Bemba Sidi Mohamed,
Christian Périgaud and
Christophe Mathé

Beilstein J. Org. Chem. 2017, 13, 251–256, doi:10.3762/bjoc.13.28

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Figure 1: Retrosynthetic pathway for the synthesis of the target carbocyclic nucleoside methylphosphonates.

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Scheme 1: Reagents and conditions: (a) (CH₃O)₂P(O)CH₃, n-BuLi, THF, −78 °C/rt, 2 h, 63%; (b) H₂, Pd/C, MeOH, ...

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Scheme 2: Reagents and conditions: (a) N⁶-bis-Boc-adenine or 2-amino-6-chloropurine, PPh₃, DIAD, THF, 0 °C to...

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Scheme 3: Reagents and conditions: (a) N⁶-bis-Boc-adenine, PPh₃, DIAD, THF, rt, 56%; (b) TFA, Cl(CH₂)₂Cl, rt,...

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Figure 2: Numbering for 14 and 16.

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Figure 3: Selected NOESY correlations for compound (+/−)-16.

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Scheme 4: Reagents and conditions: (a) i) Boc₂O, DMAP, THF, rt; ii) K₂CO₃, MeOH, 75%; (b) PPh₃, DIAD, THF, rt...

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Scheme 5: Reagents and conditions: (a) N⁶-Bz-adenine or 2-amino-6-chloropurine, PPh₃, DIAD, THF, 0 °C to rt, ...

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Published 09 Feb 2017

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Beta-hydroxyphosphonate ribonucleoside analogues derived from 4-substituted-1,2,3-triazoles as IMP/GMP mimics: synthesis and biological evaluation

Tai Nguyen Van,
Audrey Hospital,
Corinne Lionne,
Lars P. Jordheim,
Charles Dumontet,
Christian Périgaud,
Laurent Chaloin and
Suzanne Peyrottes

Beilstein J. Org. Chem. 2016, 12, 1476–1486, doi:10.3762/bjoc.12.144

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Figure 1: Previous (UA1776, UA2201 and UA2209 [7,8]) and new 1a–q phosphonate derivatives designed as potential cN...

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Scheme 1: Synthesis of (1-azido-2,5-di-O-acetyl-3-O-benzoyl-6-deoxy-6-diethylphosphono)-β-ribo-(5S)-hexofuran...

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Scheme 2: General synthetic pathway for the 1,2,3-triazolo-β-hydroxyphosphonate derivatives.

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Figure 2: Black arrow indicates ¹H,¹H-COSY correlations for compound 2. Green (C1’ and H5) and blue (H1’ and ...

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Figure 3: Arrows indicate ¹H,¹H-NOESY (blue) and ¹H,¹³C-HMBC (green) correlations for compound 3h.

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Figure 4: Arrows indicate ¹H,¹H-NOESY (blue) and ¹H,¹³C-HMBC (green) correlations for compound 3i.

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Figure 5: Inhibition of the nucleotidase activity in presence of representative triazole-based derivatives.

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Figure 6: Comparison of the docking poses obtained for two active derivatives in the substrate binding site o...

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Figure 7: Superimposition of the docking poses obtained for IMP (pink sticks), derivatives 1n (cyan sticks) a...

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Figure 8: Comparison of the docking poses obtained for three active derivatives in the substrate binding site...

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Published 18 Jul 2016

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