Jean‐Pierre Uttaro

Photoinduced Free‐Radical Preparation of Bis‐Phosphonates and Bis‐Phosphinates from Alkynes

Florian Vasco, Ilyana Gonzales, Béatrice Roy, Jean‐Pierre Uttaro et autres

A one‐pot access to alkyl‐bisphosphonates and alkyl‐bisphosphinates was developed using affordable starting materials (terminal alkynes and low‐cost photoinitiator), no metal catalyst, neither ligand, and no or little amounts of solvents. The radical reaction proceeded smoothly under UV exposure, the reaction conditions were …

fr (code pays fourni par la source)

Third‐Generation CD73 Inhibitors Based on a 4,6‐Disubstituted‐2‐Thiopyridine Scaffold

Félix Grosjean, Maria Shaldaeva, Emeline Cros‐Perrial, Céline Rodriguez et autres

Abstract Various series of 4,6‐disubstituted‐2‐thiopyridine derivatives were synthesized and evaluated as potential ecto‐5’‐nucleotidase (CD73) inhibitors. Altogether, about ninety compounds were prepared using a general synthetic pathway involving one or two steps (eventually one‐pot) procedures. Variation of the nature of the substituents in …

fr, us (code pays fourni par la source)

Purine containing carbonucleoside phosphonate analogues as novel chemotype for Plasmodium falciparum Inhibition

Bemba Sidi Mohamed, Minh Chau Nguyen, Sharon Wein, Jean‐Pierre Uttaro et autres

fr (code pays fourni par la source)

Second‐Generation CD73 Inhibitors Based on a 4,6‐Biaryl‐2‐thiopyridine Scaffold

Rayane Ghoteimi, A. Braka, Céline Rodriguez, Emeline Cros‐Perrial et autres

Various series of 4,6-biaryl-2-thiopyridine derivatives were synthesized and evaluated as potential ecto-5'-nucleotidase (CD73) inhibitors. Two synthetic routes were explored and the coupling of 4,6-disubstituted 3-cyano-2-chloro-pyridines with selected thiols allowed us to explore the structural diversity. Somehow divergent results were obtained in biological …

fr (code pays fourni par la source)

Purine Containing Carbonucleoside Phosphonate Analogues as Novel Chemotype for Plasmodium Falciparum Inhibition

Bemba Sidi Mohamed, Minh Chau Nguyen, Sharon Wein, Jean‐Pierre Uttaro et autres

fr (code pays fourni par la source)

Discovery of an L‐like Configuration for 3’‐Fluoro‐5’‐norcarbonucleoside Phosphonates as Potent Anti‐HIV Agents

Pierre‐Yves Géant, Malika Kaci, Jean‐Pierre Uttaro, Christian Périgaud et autres

Recently, we reported the racemic synthesis of 3'-fluoro-5'-norcarbocyclic nucleoside phosphonates bearing adenine as the heterocyclic base. For this study, to evaluate the antiviral activity of each enantiomer, we synthesized both enantiomers, as well as their corresponding bis(POM) prodrugs. Anti-HIV-1 evaluation against the …

fr (code pays fourni par la source)

Synthesis and Studies of Potential Inhibitors of CD73 Based on a Triazole Scaffold

Félix Grosjean, Emeline Cros‐Perrial, Abdenour Braka, Jean‐Pierre Uttaro et autres

Abstract The ecto‐5′‐nucleotidase CD73 is involved in the production of immunosuppressive adenosine in the tumoral microenvironment and recently became a validated target in immuno‐oncology. To avoid formation of CD73‐produced adenosine, several series of potential inhibitors of the target enzyme based on a …

fr (code pays fourni par la source)

4-Substituted-1,2,3-triazolo nucleotide analogues as CD73 inhibitors, their synthesis, in vitro screening, kinetic and in silico studies

Rayane Ghoteimi, A. Braka, Céline Rodriguez, Emeline Cros‐Perrial et autres

fr (code pays fourni par la source)

2-(Substituted amino)-8-azachromones from 4,6-Diaryl-2-pyridones: A Synthetic Strategy toward Compounds of Broad Structural Diversity

Steve Saulnier, Rayane Ghoteimi, Christophe Mathé, Suzanne Peyrottes et autres

3-Acetoacetyl-4,6-diaryl-2-pyridones are synthesized in three steps from chalcones and then condense with carbon disulfide to afford 8-azachromones containing a methylthio group at C2. This leaving group offers an entry point for the insertion of more complex moieties via nucleophilic substitution. For this …

fr (code pays fourni par la source)

Synthesis and Antiviral Evaluation of 3′-Fluoro-5′-norcarbocyclic Nucleoside Phosphonates Bearing Uracil and Cytosine as Potential Antiviral Agents

Pierre‐Yves Géant, Jean‐Pierre Uttaro, Christian Périgaud, Christophe Mathé

Carbocyclic nucleoside analogues are an essential class of antiviral agents and are commonly used in the treatment of viral diseases (hepatitis B, AIDS). Recently, we reported the racemic synthesis and the anti-human immunodeficiency virus activities (HIV) of 3'-fluoro-5'-norcarbocyclic nucleoside phosphonates bearing purines …

fr (code pays fourni par la source)

Straightforward chemical desymmetrisation of cis-(±)-4-O-protected-cyclopent-2-enol using resolving agents on column chromatography

Bemba Sidi Mohamed, Suzanne Peyrottes, Jean‐Pierre Uttaro, Christophe Mathé

A simple and efficient procedure for the separation of cis-(+)- and cis-(−)-4-O-protected-cyclopent-2-enol, from the corresponding racemic mixture as starting material and using resolving agents, is described. The separation of diasteroisomers was accomplished by flash silica gel column chromatography. The enantiomers cis-(+)- and …

fr (code pays fourni par la source)

Synthesis of Substituted 5′‐Aminoadenosine Derivatives and Evaluation of Their Inhibitory Potential toward CD73

Rayane Ghoteimi, Rahila Rahimova, Félix Grosjean, Emeline Cros‐Perrial et autres

Derivatives of 5'-aminoadenosine containing methyl carboxylate, methyl phosphonate, gem-bisphosphonate, bis(methylphosphonate), and α-carboxylmethylphosphonate or phosphonoacetate moieties were synthesized from key intermediate 5'-aminonucleoside. These nucleotide analogues were envisaged as 5'-mono- or diphosphate nucleoside mimics. All compounds were evaluated for CD73 inhibition in a cell-based …

fr (code pays fourni par la source)