Nicolas Gouault
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View article: A Straightforward Access to Enantiopure 4‐Hydroxy‐pipecolic Acid Peptidomimetics by aza‐Prins Cyclization/LiNTf <sub>2</sub> ‐Promoted Aminolysis of Lactones
A Straightforward Access to Enantiopure 4‐Hydroxy‐pipecolic Acid Peptidomimetics by aza‐Prins Cyclization/LiNTf <sub>2</sub> ‐Promoted Aminolysis of Lactones Open
Peptidomimetics, that can take advantage of bioavailability and metabolic stability, are considered as an important class of molecules and constitute thus a large research field in medicinal chemistry. With the aim of obtaining constrained…
View article: Synthesis and biological studies on ovarian cancer cells of new heterocyclic molecules inspired by MIM1, an inhibitor of the anti-apoptotic protein Mcl-1
Synthesis and biological studies on ovarian cancer cells of new heterocyclic molecules inspired by MIM1, an inhibitor of the anti-apoptotic protein Mcl-1 Open
Research on new and potent inhibitors of anti-apoptotic proteins is a very active and promising topic in bioorganic and medicinal chemistry.
View article: Synthesis of 4-hydroxypiperidines containing a quaternary stereocenter by aza-Prins cyclization
Synthesis of 4-hydroxypiperidines containing a quaternary stereocenter by aza-Prins cyclization Open
The diastereoselective synthesis of 4-hydroxypiperidines bearing a tetrasubstituted carbon stereocenter at C4 by aza-Prins cyclization is presented. These motifs are relevant because they are present in a considerable number of drugs.
View article: One‐Pot Double Cyclizations Involving an Aza‐Prins Process
One‐Pot Double Cyclizations Involving an Aza‐Prins Process Open
Piperidine derivatives are highly abundant in natural products and pharmaceutically relevant compounds. Aza‐Prins cyclization has emerged as a step‐ atom‐economical and stereoselective method for the preparation of such azacycles. The poss…
View article: Synthesis and Chemoinformatic Analysis of Fluorinated Piperidines as 3D Fragments for Fragment-Based Drug Discovery
Synthesis and Chemoinformatic Analysis of Fluorinated Piperidines as 3D Fragments for Fragment-Based Drug Discovery Open
The concise synthesis of a small library of fluorinated piperidines from readily available dihydropyridinone derivatives has been described. The effect of the fluorination on different positions has then been evaluated by chemoinformatic t…
View article: Aza‐Prins Cyclization on Ketones to Access Piperidines with Tetrasubstituted Carbon Stereocenters
Aza‐Prins Cyclization on Ketones to Access Piperidines with Tetrasubstituted Carbon Stereocenters Open
The aza‐Prins cyclization in presence of a variety of aliphatic, aromatic, and heterocyclic ketones is disclosed. The developed method allows an access to diverse C‐2 functionalized piperidines, bearing a tetrasubstituted or spiranic carbo…
View article: Accessing spiropiperidines from dihydropyridones through tandem triflation–allylation and ring-closing metathesis (RCM)
Accessing spiropiperidines from dihydropyridones through tandem triflation–allylation and ring-closing metathesis (RCM) Open
We report an approach to build 2-spiropiperidine moieties starting from dihydropyridones through a tandem triflation–allylation reaction followed by ring-closing metathesis and then Pd-catalyzed functionalization.
View article: Structure Activity Relationship Studies around DB18, a Potent and Selective Inhibitor of CLK Kinases
Structure Activity Relationship Studies around DB18, a Potent and Selective Inhibitor of CLK Kinases Open
Three series of our lead CLK1 inhibitor DB18 have been designed, synthetized and tested against CLKs and DYRK1A kinases. Their cytotoxicity was subsequently measured on seven representative cancer cell lines. Guided by docking experiments,…
View article: Irreversible inhibitors of the proline racemase unveil innovative mechanism of action as antibacterial agents against <i>Clostridioides difficile</i>
Irreversible inhibitors of the proline racemase unveil innovative mechanism of action as antibacterial agents against <i>Clostridioides difficile</i> Open
Proline racemases (PRAC), catalyzing the l ‐proline and d ‐proline interconversion, are essential factors in eukaryotic pathogens such as Trypanosoma cruzi , Trypanosoma vivax , and Clostridioides difficile . If the discovery of irreversib…
View article: Structural and molecular bases to IRE1 activity modulation
Structural and molecular bases to IRE1 activity modulation Open
The Unfolded Protein response is an adaptive pathway triggered upon alteration of endoplasmic reticulum (ER) homeostasis. It is transduced by three major ER stress sensors, among which the Inositol Requiring Enzyme 1 (IRE1) is the most evo…
View article: Synthesis of Novel Cyclic Nitrones with <i>gem</i>‐Difluoroalkyl Side Chains Through Cascade Reactions
Synthesis of Novel Cyclic Nitrones with <i>gem</i>‐Difluoroalkyl Side Chains Through Cascade Reactions Open
New five‐membered cyclic nitrones with gem ‐difluoroalkyl groups in γ‐position have been prepared by a 3‐step sequence starting from propargylic alcohols. This domino process involves a base‐mediated isomerization reaction to enones, which…
View article: CCDC 1941252: Experimental Crystal Structure Determination
CCDC 1941252: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 1941250: Experimental Crystal Structure Determination
CCDC 1941250: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 1941251: Experimental Crystal Structure Determination
CCDC 1941251: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Designed mono- and di-covalent inhibitors trap modeled functional motions for Trypanosoma cruzi proline racemase in crystallography
Designed mono- and di-covalent inhibitors trap modeled functional motions for Trypanosoma cruzi proline racemase in crystallography Open
Chagas disease, caused by Trypanosoma cruzi, affects millions of people in South America and no satisfactory therapy exists, especially for its life threatening chronic phase. We targeted the Proline Racemase of T. cruzi, which is present …
View article: Gold-Catalyzed Synthesis of Substituted 3-Trifluoromethylpyrroles from Mesylated Amino Trifluoromethylpropargylic Alcohols
Gold-Catalyzed Synthesis of Substituted 3-Trifluoromethylpyrroles from Mesylated Amino Trifluoromethylpropargylic Alcohols Open
A series of substituted 3-trifluoromethylpyrroles was obtained from trifluoromethylamino-ynol derivatives via a gold-catalyzed cyclization. Using fluorinated starting materials, after mesylation, allowed for the desired compounds to be obt…
View article: Isolation and Structure Identification of Novel Brominated Diketopiperazines from Nocardia ignorata—A Lichen-Associated Actinobacterium
Isolation and Structure Identification of Novel Brominated Diketopiperazines from Nocardia ignorata—A Lichen-Associated Actinobacterium Open
Actinobacteria are well known for their potential in biotechnology and their production of metabolites of interest. Lichens are a promising source of new bacterial strains, especially Actinobacteria, which afford a broad chemical diversity…
View article: CCDC 1474017: Experimental Crystal Structure Determination
CCDC 1474017: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: FLUOROUS SUPPORTED SYNTHESIS OF PYRAZOLONE DERIVATIVES FROM ALLYLIC ALCOHOLS USING A PALLADIUM-CATALYZED STRATEGY
FLUOROUS SUPPORTED SYNTHESIS OF PYRAZOLONE DERIVATIVES FROM ALLYLIC ALCOHOLS USING A PALLADIUM-CATALYZED STRATEGY Open
Ten substituted pyrazolone derivatives were easily synthesized from perfluorinated allylic alcohols, via a straightforward two steps reaction involving a Heck-coupling/isomerization reaction and subsequent condensation of hydrazines. This …