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Pierre Vogel

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Related publications (98)

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Identification of new FK866 analogues with potent anticancer activity against pancreatic cancer

Pierre Vogel, Somi Reddy Majjigapu, Jianfei Bai

Pancreatic ductal adenocarcinoma (PDAC) is one of the most lethal diseases for which chemotherapy has not been very successful yet. FK866 ((E)-N-(4-(1-benzoylpiperidin-4-yl)butyl)-3-(pyridin-3-yl)acrylamide) is a well-known NAMPT (nicotinamide phosphoribos ...

ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER2022

One-pot synthesis of 1-aryl-3-methyl-1,3-dienes using methallyl(trimethyl)silane and aldehydes and their low temperature (Z)->(E) isomerization induced by sulfur dioxide

Pierre Vogel

2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1-sulfonyl fluorides give 1.3-(E) and (Z)-dienes. Their (Z) --> (E) isomerization b ...

2005

Sulfur dioxide-mediated syntheses of polyfunctional alkenes and (E,Z)- and (E,E)-2,4-dien-1-ones

Pierre Vogel, Laure Bouchez, Cotinica Craita

Efficient methods for the stereoselective synthesis of polyfunctional (E)- and (2)-alkenes and conjugated (EE)- and (E,2)-dienones are presented. They rely upon one-pot, four-component processes that condense 1-oxy-1,3-dienes, silyl enol ethers, SO2, and c ...

2005

Functionalized pyrrolidines as alpha-mannosidase inhibitors and growth inhibitors of human glioblastoma and melanoma cells

Pierre Vogel, Sandrine Gerber, Sylvain Favre, Hélène Fiaux

New substituted pyrrolidine-3,4-diol derivatives were prepared from D-(-)- and L-(+)-phenyl glycinol. The influence of the configuration and the substitution of the lateral side chain of these derivatives on the inhibition of 25 commercial glycosidases wer ...

2005

Umpolung with Sulfur Dioxide: Carbon-Carbon Cross-Coupling of Electron-Rich 1,3-Dienes and Alkenes; Application to the Enantioselective Synthesis of Long-Chain Polyketide Fragments

Pierre Vogel, Maris Turks, Claudia Jana Exner

At low temperature and in the presence of an acid catalyst, sulfur dioxide undergoes hetero-Diels-Alder additions with 1-oxy-1,3-dienes, giving unstable sultines, which are ionized into zwitterionic species and react as 1-oxyallylic cation intermediates (U ...

2009

Rational Design of 4-Aryl-1,2,3-Triazoles for Indoleamine 2,3-Dioxygenase 1 Inhibition

Pierre Vogel, Somi Reddy Majjigapu

Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used co ...

2012

The spirocyclopropyl moiety as a methyl surrogate in the structure of L-fucosidase and L-rhamnosidase inhibitors

Pierre Vogel

Nitrogen-in-the-ring analogues of L-fucose and L-rhamnose were prepared, which feature a spirocyclopropyl moiety in place of the methyl group of the natural sugar. The synthetic route involved a titanium-mediated aminocyclopropanation of a glycononitrile a ...

2009

Silyl methallylsulfinates: efficient and powerful agents for the chemoselective silylation of alcohols, polyols, phenols and carboxylic acids

Pierre Vogel, Loay Awad, Cotinica Craita, Xiaogen Huang

Alcohols, phenols and carboxylic acids are silylated with very good yields in the presence of silyl methallylsulfinates under non- basic conditions and with the formation of volatile co-products. ...

Royal Society of Chemistry2005

C(1 -> 4)-linked disaccharides through carbonylative Stille cross-coupling

Pierre Vogel, Peter Steunenberg

A tinglucal tributyl[4,6-O-bis(t-butyl)silylidene-3-O-tris(isopropyl)silyl]tin 7 and a triflate derived from isolevoglucosenone (1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate 10 undergo the carbonylative Stille conden ...

2005

Detailed analysis and follow-up studies of a high-throughput screening for indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors

Pierre Vogel, Gerardo Turcatti, Marc Chambon, Somi Reddy Majjigapu

Indoleamine 2,3-dioxygenase 1 (IDO1) is a key regulator of immune responses and therefore an important therapeutic target for the treatment of diseases that involve pathological immune escape, such as cancer. Here, we describe a robust and sensitive high-t ...

Elsevier France-Editions Scientifiques Medicales Elsevier2014

Synthesis of (E,Z)-1-Alkoxy-3-acyloxy-2-methylpenta-1,3-dienes via Danishefsky-Type Dienes or O-Acylation of Enones

Pierre Vogel, Maris Turks, Claudia Jana Exner

1-Alkoxy-2-methyl-3-acyloxy-(E,E)-penta-1,3-dienes have been prepared applying among others a modified Danishefsky's general method, including chiral, racemic, and achiral derivatives. ...

2009

Chemoselective C-H Bond Activation: Ligand and Solvent Free Iron-Catalyzed Oxidative C-C Cross-Coupling of Tertiary Amines with Terminal Alkynes. Reaction Scope and Mechanism

Pierre Vogel

FeCl2 catalyzes the oxidative C-C cross-coupling of tertiary amines with terminal alkynes into propargylamines using (t-BuO)2 as oxidant. The reaction can be applied to aromatic and aliphatic amines and alkynes without solvent. High chemoselectivity for am ...

2009

C-linked disaccharide analogue of the Thomsen-Friedenreich (T)-epitope alpha-O-conjugated to L-serine

Pierre Vogel, Loay Awad

Condensation of a silylated beta-D-galactopyranosylaldehyde (3) with isolevoglucosenone (4) in the presence of Et(2)AII provided bicyclic enone 5. Subsequent addition of BnNHOMe gave adduct 6, which was converted into 4-O-acetyl-1,6-anhydro-3-C-[ R)1.3,4,5 ...

2005

Anti-cancer activity of 5-O-alkyl 1,4-imino-1,4-dideoxyribitols

Pierre Vogel

New derivatives of 1,4-dideoxy-1,4-imino-D-ribitol have been prepared and evaluated for their cytotoxicity on solid and haematological malignancies. 1,4-Dideoxy-5-O-[(9Z)-octadec-9-en-1-yl]-1,4-imino-Dribitol (13, IC50 similar to 2 mu M) and its C-18-analo ...

2011

Synthesis of D- and L-erythro 1,5-dithiopent-1-enopyranoside sulfonium salts and their evaluation as glycosidase inhibitors

Pierre Vogel

A series of sulfonium salts derived from 1,5-dithiopent-1-enopyranosides was prepared in a three-step sequence from protected D- and L-erythrofuranoses. The key step is the nucleophilic displacement of a leaving group by a sulfur atom of carbohydrate-deriv ...

2009

New 1-amino-1-deoxy- and 2-amino-2-deoxy-polyhydroxyazepanes: synthesis and inhibition of glycosidases

Pierre Vogel, Eliazar Rodriguez Garcia

Eight new seven-membered ring iminoalditols, displaying an amino group and a hydroxymethyl group on the ring, have been synthesized from D-arabinose via epoxidation of a protected azacycloheptene and subsequent nucleophilic opening. Three of them show a po ...

2005

Palladium-catalyzed desulfitative Mizoroki-Heck couplings of sulfonyl chlorides with mono- and disubstituted olefins: Rhodium-catalyzed desulfitative heck-type reactions under phosphine- and base-free conditions

Pierre Vogel

New conditions have been found for the desulfitative Mizoroki-Heck arylation and trifluoromethylation of mono- and disubustituted olefins with arenesulfonyl and trifluoromethanesulfonyl chlorides. Thus (E)1,2-disubstituted alkenes with high stereoselectivi ...

2005

Use of sultines in the asymmetric synthesis of polypropionate antibiotics

Pierre Vogel, Maris Turks, Laure Bouchez, Cotinica Craita, Xiaogen Huang, Freddy Fonquerne

At low temperature and in the presence of an acid catalyst, SO2 adds to 1,3-dienes equilibrating with the corresponding 3,6-dihydro-1,2-oxathiin-2-oxides (sultines). These compounds are unstable above -60 degrees C and equilibrate with the more stable 2,5- ...

De Gruyter2008

Preparation and synthetic applications of 8-oxabicyclo[3.2.1]oct-6-en-3-one derivatives

Pierre Vogel, Sandrine Gerber, Sylvain Favre

The development of efficient routes to multi gram quantities of chiral synthons is a key issue in total synthesis of natural products and analogues. The conformationally defined and rigid 8-oxabicyclo[3.2.1]oct-6-en-3-one template appears as an appealing s ...

2008

Noniterative approach to the total asymmetric synthesis of 15-carbon polyketides and analogs with high stereodiversity

Pierre Vogel, Sandrine Gerber, Marc-Etienne Schwenter, Kai Torsten Meilert

Starting from inexpensive furan and furfuryl alcohol, a noniterative approach to the synthesis of pentadeca-1,3,5,7,9,11,13,15-octols and their derivatives has been developed. The method relies upon the double [4+3]-cycloaddition of 1,1,3-trichloro-2-oxyla ...

2005