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Pierre Vogel

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Related publications (99)

BCl3-Mediated Ene Reaction of Sulfur Dioxide and Unfunctionalized Alkenes

Pierre Vogel, Dean Markovic, Chandra Mouleeswara Rao Volla

The first ene reactions of SO2 and unfunctionalized alkenes are reported. Calculations suggest that the endergonic ene reactions of SO2 with alkenes can be used to generate beta,gamma-unsaturated sulfinyl and sulfonyl compounds. Indeed, in the presence of ...

2010

Stereoselective syntheses of polyhydroxylated azepane derivatives from sugar-based epoxyamides. Part 1: synthesis from D-mannose

Pierre Vogel, Claudia Bello

An approach to the synthesis of polyhydroxyazepane derivatives from sugar-based epoxyamides or epoxyalcohols, in which the total regioselective epoxide opening by nitrogen nucleophiles is the key step, is described. Thus, novel polyhydroxyazepane carboxami ...

2010

Synthesis, Biological Evaluation and Docking Studies of Casuarine Analogues: Effects of Structural Modifications at Ring B on Inhibitory Activity Towards Glucoamylase

Pierre Vogel, Claudia Bello

We report the total synthesis of a series of pyrrolizidine analogues of casuarine (1) and their 6-O-alpha-glucoside derivatives. The synthetic strategy is based on a totally regio- and stereoselective 1,3-dipolar cycloaddition of suitably substituted alken ...

2010

Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as alpha-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies

Pierre Vogel, Claudia Bello, Bernard Sordat, Marc Dupuis

Novel alpha-mannosidase inhibitors of the type (2R,3R,4S)-2-({[(1R)-2- hydroxy-1-arylethyl]amine}methyl) pyrrolidine-3,4-diol have been prepared and assayed for their anticancer activities. Compound 30 with the aryl group = 4-trifluoromethylbiphenyl inhibi ...

2010

Synthesis of new oxathiazinane dioxides and their in vitro cancer cell growth inhibitory activity

Pierre Vogel, Claudia Bello, Matthias Baud, Françoise Borcard

New oxathiazinane dioxides have been derived from D- and L-serine and tested for their in vitro cell growth inhibitory activity toward SKBR3 breast cancer cells. (5R)-5-(4-(4'-Bromomethyl)phenyl)benzyloxymethyl-[1,3,4]-oxathiazinane- 3,3-dioxide showed a c ...

2010

Structural Insights into the Specificity of Xyn10B from Paenibacillus barcinonensis and Its Improved Stability by Forced Protein Evolution

Pierre Vogel

Paenibacillus barcinonensis is a soil bacterium bearing a complex set of enzymes for xylan degradation, including several secreted enzymes and Xyn10B, one of the few intracellular xylanases reported to date. The crystal structure of Xyn10B has been determi ...

2010

Synthesis and glycosidase inhibitory activity of 1-amino-3,6-anhydro-1-deoxy-D-sorbitol derivatives

Pierre Vogel, Claudia Bello

3,6-Anhydro-1-(aryl or alkylamino)-1-deoxy-D-sorbitol derivatives have been prepared in four steps from isosorbide, a by-product from the starch industry. The inhibitory activities of these new compounds have been evaluated towards 13 glycosidases. A first ...

2010

Rational Design of Indoleamine 2,3-Dioxygenase Inhibitors

Pierre Vogel, Loay Awad, Olivier Michielin

Indoleamine 2,3-dioxygenase (IDO) is an important therapeutic target for the treatment of diseases such as cancer that involve pathological immune escape. We have used the evolutionary docking algorithm EADock to design new inhibitors of this enzyme. First ...

2010

Design and synthesis of acetamido tri- and tetra-hydroxyazepanes: Potent and selective beta-N-acetylhexosaminidase inhibitors

Pierre Vogel, Claudia Bello

A series of seven-membered iminosugars bearing an acetamido group beta- or gamma- to the endocyclic nitrogen have been synthesized via simple transformations of previously described polysubstituted azepanes. These tetra- and trihydroxylated acetamido azepa ...

2009

Ligandless Iron-Catalyzed Desulfinylative C-C Allylation Reactions using Grignard Reagents and Alk-2-enesulfonyl Chlorides

Pierre Vogel, Dean Markovic, Chandra Mouleeswara Rao Volla

Alk-2-enesulfonyl chlorides 1-4 were synthesized by the BCl3-promoted ene reaction of alkenes with SO2. These sulfonyl chlorides were then used as electrophilic partners in iron-catalyzed desulfinylative cross-coupling reactions with different Grignard rea ...

2009

Synthesis of Optically Active 5-Alkoxy-6-methylcyclohex-2-en-1-ones and 4-Alkoxy-5-methylcyclopent-1-enyl Benzoate

Pierre Vogel, Maris Turks

The reaction of (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-ol benzoate with allyltrimethylsilane in SO,- and in the presence of a catalytic amount of Tf2NTMS gives a silyl sulfinate intermediate that furnishes (-)-(6Z,1'S,4S,5S)-5-methyl- ...

American Chemical Society2009

A Short and Convenient Synthesis of 1-Deoxymannojirimycin (DMJ) and N-oxy-Analogues from D-Fructose

Pierre Vogel, Sandrine Gerber, Claudia Bello

The ketonitrone 8 was prepared from D-fructose as an inexpensive starting material, and was used in a stereoselective synthesis of 1-deoxymannojirimycin (4), its previously unknown N-hydroxy analogue 15, as well as the polyhydroxylated ketonitrone 14. The ...

2009

Palladium-catalyzed desulfinylative C–C allylation of Grignard reagents and enolates using allylsulfonyl chlorides and esters

Pierre Vogel, Chandra Mouleeswara Rao Volla

2-Methylprop-2-ene-, prop-2-ene-, 1-methylprop-2-ene-, and (E)-but-2-enesulfonyl chlorides have been used as electrophilic partners in desulfinylative palladium- catalyzed C–C coupling with Grignard reagents and sodium salts of dimethyl malonate and methyl ...

2009

Synthesis and Conformational Analysis of (alpha-D-Galactosyl)phenylmethane and alpha-,beta-Difluoromethane Analogues: Interactions with the Plant Lectin Viscumin

Pierre Vogel, Maria Kolympadi

alpha-D-Galactosyl)phenylmethane (1). (alpha- and beta-D-galactosyl)-(difluoro)phenylmethane (2 and 3) have been prepared and their conformations in solution were described by using a combination of force-field calculations and NMR spectroscopic studies. G ...

2009

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

Pierre Vogel, Claudia Bello

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

Depletion of the intracellular coenzyme NAD plus in activated T-cells ameliorates experimental autoimmune encephalomyelitis

Pierre Vogel, Bernard Sordat

2009

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

Pierre Vogel, Claudia Bello

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

Synthesis of novel pyrrolidine 3,4-diol derivatives as inhibitors of alpha-L-fucosidases

Pierre Vogel, Yolanda Vera-Ayoso, Inmaculada Robina, Claudia Bello

The stereoselective synthesis of new 3,4-dihydroxypyrrolidine derivatives starting from D-mannose, D-ribose and L-fucose is presented. Two synthetic strategies employing organometallic addition to hemiacetalic sugars followed by selective nucleophilic disp ...

2009

Desulfinylation of Prop-2-enesulfinic Acid: Experimental Results and Mechanistic Theoretical Analysis

Pierre Vogel, Dean Markovic

The potential energy surfaces of the desulfinylation of prop-2-enesulfinic acid (13) in CH2Cl2 solution at -15 degrees C have been explored by quantum calculations and analyzed with kinetic data obtained for the reaction in absence or presence of additives ...

2009

Derivatives of dihydroxypyrrolidine as anti- cancer compounds

Pierre Vogel, Claudia Bello

The present invention relates to derivatives of dihydroxypyrrolidine useful in the treatment of cancer. The invention further relates to a process for making the compounds. The compounds are inhibitors of alpha mannosidase, and possibly, also inhibit nicot ...

2009

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