Magali Szlosek-Pinaud - Academia.edu (original) (raw)
Papers by Magali Szlosek-Pinaud
ChemInform, 1998
Acetogenins of Annonaceae. Part 65. Glaucabellin and Glaucaflorin, Two Acetogenins from Annona gl... more Acetogenins of Annonaceae. Part 65. Glaucabellin and Glaucaflorin, Two Acetogenins from Annona glauca. -The relative stereochemistry of new glaucabellin (I) and glaucaflorin (II), isolated from the seeds of the title species, is elucidated by spectral analyses and chemical methods. -(WAECHTER, A.-I.; SZLOSEK, M.; HOCQUEMILLER, R.; LAURENS, A.; CAVE, A.; Phytochemistry 48 (1998) 1, 141-145; Lab. Pharmacogn., CNRS, Fac. Pharm., Univ. Paris-Sud, F-92296 Chatenay-Malabry, Fr.; EN)
ChemPlusChem, 2012
ABSTRACT The winning combination: A new and promising 18F-labeled RGD derivative has been efficie... more ABSTRACT The winning combination: A new and promising 18F-labeled RGD derivative has been efficiently prepared by exploiting the advantages of “click” chemistry and a one-step labeling protocol where a silicon-based building blocks was used (see figure). This derivative could be a new starting point for improved visualization of αvβ3-positive tumors by positron emission tomography.
Tetrahedron, 2014
ABSTRACT This work reports on a new intermolecular C–C coupling reaction between electron rich ar... more ABSTRACT This work reports on a new intermolecular C–C coupling reaction between electron rich arenes and benzylic alcohols or ethers, catalysed by gold(III) salts, or other catalysts such as gold(I) and iron (III), and its application to the regio- and stereoselective synthesis of procyanidins dimers B1 and B3.
Tetrahedron Letters, 2010
Different thymidine derivatives bearing either an iodoaryl moiety at the 5 0 position or a dialky... more Different thymidine derivatives bearing either an iodoaryl moiety at the 5 0 position or a dialkylsilyl group at the 3 0 position have been efficiently synthesized as precursors for carbon-11 or fluorine-18 labeling, respectively. Furthermore, iodoarylated thymidine derivatives have been incorporated into oligonucleotides giving an original way to label them with carbon-11.
Tetrahedron Letters, 2003
A novel one-pot palladium-catalyzed cascade between 2-iodophenol, methyl bromomethylacrylate and ... more A novel one-pot palladium-catalyzed cascade between 2-iodophenol, methyl bromomethylacrylate and an arylboronic acid provides an efficient access to heterocycles possessing the 3,3-disubstituted-2,3-dihydrobenzofuran skeleton via allylation/carbopalladation/Suzuki cross-coupling.
Tetrahedron, 2007
Reactions. -(SZLOSEK-PINAUD, M.; DIAZ, P.; MARTINEZ, J.; LAMATY*, F.; Tetrahedron 63 (2007) 16, 3... more Reactions. -(SZLOSEK-PINAUD, M.; DIAZ, P.; MARTINEZ, J.; LAMATY*, F.; Tetrahedron 63 (2007) 16, 3340-3349; Lab. Amino-Acides Pept. Prot., Fac. Pharm.,
Phytochemistry, 1998
The seeds of Annona 9lauca have yielded four Annonaceous acetogenins. Two of them, glaucabellin a... more The seeds of Annona 9lauca have yielded four Annonaceous acetogenins. Two of them, glaucabellin and glaucaflorin, whose chemical structure was deduced by spectral and chemical methods, are new. ~'~
New Journal of Chemistry, 2000
... Magali Szlosek, Jean-François Peyrat, Christophe Chaboche, Xavier Franck, Reynald Hocquemille... more ... Magali Szlosek, Jean-François Peyrat, Christophe Chaboche, Xavier Franck, Reynald Hocquemiller and Bruno Figadère*. Laboratoire de Pharmacognosie [CNRS UPRES-A (BIOCIS)], Université de Paris-Sud ... 17, Since 1998: (a) SE Schaus, J. Branalt and EN Jacobsen, J. Org. ...
Molecules, 2013
The methyl transfer reaction from activated monomethyltin, via a modified Stille coupling reactio... more The methyl transfer reaction from activated monomethyltin, via a modified Stille coupling reaction, was studied under "ligandless" conditions on fully deprotected 5'-modified nucleosides and one dinucleotide. The reaction was optimized to proceed in a few minutes and quantitative yield, even under dilute conditions, thus affording a rapid and efficient new method for oligonucleotide labelling with carbon-11.
Journal of the American Chemical Society, 2001
The mycolactones were isolated in 1999 by Small and co-workers 1 from Mycobacterium ulcerans, the... more The mycolactones were isolated in 1999 by Small and co-workers 1 from Mycobacterium ulcerans, the causative pathogen of Buruli ulcer. This disease is characterized by the formation of large, painless, necrotic ulcers and the lack of an acute inflammatory response. Evidence from animal studies suggests that the mycolactones are directly responsible for the observed pathology, and they have attracted considerable attention for their highly potent apoptotic activity as well as for being the first examples of polyketide macrolides to be isolated from a human pathogen. The gross structure of these natural products was elucidated through 2D NMR experiments. 2 Via a combined approach employing both an NMR database and the preparation of model compounds, we recently established the relative and absolute configuration of the mycolactone core structure ( ). 3 Extending the newly developed universal NMR database concept in chiral solvents 4 to a proton NMR database, we report the complete structure of the mycolactones in this Communication.
The Journal of Organic Chemistry, 1998
ABSTRACT TMSOF 2-[(trimethylsilyl)oxy]furan has been used in an enantioselective aldol reaction f... more ABSTRACT TMSOF 2-[(trimethylsilyl)oxy]furan has been used in an enantioselective aldol reaction for the first time. Indeed, addition of TMSOF to achiral aldehydes, in the presence (R)-1,1‘-bi-2-naphthol (Binol), gave the corresponding butenolides with moderate diastereomeric ratios (dr = 60%) and ee's between 60 and 90%. Application of this reaction to the total synthesis of annonaceous muricatacin in only two steps (in regards to the numerous multistep syntheses published so far) illustrated the efficiency of this strategy.
![Research paper thumbnail of 11 C Click Chemistry Using [ 11 C]Methyl Azide: Simplified, Versatile, and Practical Alternative Access to [ 11 C]Nucleosides and [ 11 C]Oligonucleotides for PET Imaging](https://attachments.academia-assets.com/42025660/thumbnails/1.jpg)
](European Journal of Organic Chemistry, 2013
This communication reports the simplified formation of methyl azide and its use in the Huisgen cy... more This communication reports the simplified formation of methyl azide and its use in the Huisgen cycloaddition for the rapid, efficient, and selective labeling of modified nucleosides and oligonucleotides. The transposition to radioactive
Current Medicinal Chemistry, 2008
Positron Emission Tomography has become a powerful scientific and clinical tool probing biochemic... more Positron Emission Tomography has become a powerful scientific and clinical tool probing biochemical processes in the human body. Their clinical applications have proven to be vital in the evaluation and diagnosis of diseases. This is due, in large part, to advances in instrumentation and synthetic chemistry. Carbon-11 is a valuable radionuclide in PET as it virtually permits the synthesis of radiolabelled versions of any compound of interest. The syntheses with carbon-11 present several features: limited number of labelled precursors, sub-micromolar amounts of the starting materials, and a need for the introduction of the radioisotope as late as possible in the synthesis. All of these reasons have restricted complex radiosyntheses. The short half-life of carbon-11 (20.4 min) requires the rapid preparation and purification of carbon-11 labelled molecules. Those have to be carried out immediately before use from cyclotron produced precursors ([ 11 C]CO2, [ 11 C]CO, [ 11 C]CH4) or reagents rapidly prepared from them ([ 11 C]CH3I, [ 11 C]COCl2, [ 11 C]HCN). As a consequence carbon-11 has been underused compared to fluorine-18. However, because of the increasing molecular complexity and diversity of biologically active compounds, there is a need for new methodologies giving access in short time and high yield to radioactive 11 C-probes. The aim of this review is to emphasize the methodologies used in this field and to give a comprehensive overview of the numerous advances, which occurred over the past decade. In addition, for each labelling technique or reaction reported, a special attention has been brought to classify the applications in function of the targeted medical domain.
ChemMedChem, 2014
A novel SiX-dipropargyl glycerol scaffold (X: H, F, or (18) F) was developed as a versatile prost... more A novel SiX-dipropargyl glycerol scaffold (X: H, F, or (18) F) was developed as a versatile prosthetic group that provides technical advantages for the preparation of dimeric radioligands based on silicon fluoride acceptor pre- or post-labeling with fluorine-18. Rapid conjugation with the prosthetic group takes place in microwave-assisted click conjugation under mild conditions. Thus, a bivalent homodimeric SiX-dipropargyl glycerol derivatized radioligand, [(18) F]BMPPSiF, with enhanced affinity was developed by using click conjugation. High uptake of the radioligand was demonstrated in 5-HT1A receptor-rich regions in the brain with positron emission tomography. Molecular docking studies (rigid protein-flexible ligand) of BMPPSiF and known antagonists (WAY-100635, MPPF, and MefWAY) with monomeric, dimeric, and multimeric 5-HT1A receptor models were performed, with the highest G score obtained for docked BMPPSiF: -6.766 as compared with all three antagonists on the monomeric model. Multimeric induced-fit docking was also performed to visualize the comparable mode of binding under in vivo conditions, and a notably improved G score of -8.455 was observed for BMPPSiF. These data directly correlate the high binding potential of BMPPSiF with the bivalent binding mode obtained in the biological studies. The present study warrants wide application of the SiX-dipropargyl glycerol prosthetic group in the development of ligands for imaging with enhanced affinity markers for specific targeting based on peptides, nucleosides, and lipids.
![Research paper thumbnail of Silicon-Based Chemistry: An Original and Efficient One-Step Approach to [18F]-Nucleosides and [18F]-Oligonucleotides for PET Imaging](https://attachments.academia-assets.com/42025662/thumbnails/1.jpg)
](Chemistry - A European Journal, 2011
Positron emission tomography (PET) is a powerful molecular-imaging technique for physiological an... more Positron emission tomography (PET) is a powerful molecular-imaging technique for physiological and biological investigations in various areas, such as oncology, cardiology, and neurosciences, as well as for drug development. Due to
Bioorganic & Medicinal Chemistry Letters, 2003
Angewandte Chemie International Edition, 2000
ABSTRACT A stepwise addition of 2-trimethylsilyloxyfuran (2-TMSOF) to achiral aldehydes in the pr... more ABSTRACT A stepwise addition of 2-trimethylsilyloxyfuran (2-TMSOF) to achiral aldehydes in the presence of a chiral Lewis acid, such as a (R)-(1,1'-bi-2- naphthol)2Ti complex, affords the corresponding butenolides [Eq. (1)] in good yields with good to excellent ee values (70 to 96% ee). This is the first reported catalytic asymmetric autoinductive aldol reaction.
ChemInform, 1998
Acetogenins of Annonaceae. Part 65. Glaucabellin and Glaucaflorin, Two Acetogenins from Annona gl... more Acetogenins of Annonaceae. Part 65. Glaucabellin and Glaucaflorin, Two Acetogenins from Annona glauca. -The relative stereochemistry of new glaucabellin (I) and glaucaflorin (II), isolated from the seeds of the title species, is elucidated by spectral analyses and chemical methods. -(WAECHTER, A.-I.; SZLOSEK, M.; HOCQUEMILLER, R.; LAURENS, A.; CAVE, A.; Phytochemistry 48 (1998) 1, 141-145; Lab. Pharmacogn., CNRS, Fac. Pharm., Univ. Paris-Sud, F-92296 Chatenay-Malabry, Fr.; EN)
ChemPlusChem, 2012
ABSTRACT The winning combination: A new and promising 18F-labeled RGD derivative has been efficie... more ABSTRACT The winning combination: A new and promising 18F-labeled RGD derivative has been efficiently prepared by exploiting the advantages of “click” chemistry and a one-step labeling protocol where a silicon-based building blocks was used (see figure). This derivative could be a new starting point for improved visualization of αvβ3-positive tumors by positron emission tomography.
Tetrahedron, 2014
ABSTRACT This work reports on a new intermolecular C–C coupling reaction between electron rich ar... more ABSTRACT This work reports on a new intermolecular C–C coupling reaction between electron rich arenes and benzylic alcohols or ethers, catalysed by gold(III) salts, or other catalysts such as gold(I) and iron (III), and its application to the regio- and stereoselective synthesis of procyanidins dimers B1 and B3.
Tetrahedron Letters, 2010
Different thymidine derivatives bearing either an iodoaryl moiety at the 5 0 position or a dialky... more Different thymidine derivatives bearing either an iodoaryl moiety at the 5 0 position or a dialkylsilyl group at the 3 0 position have been efficiently synthesized as precursors for carbon-11 or fluorine-18 labeling, respectively. Furthermore, iodoarylated thymidine derivatives have been incorporated into oligonucleotides giving an original way to label them with carbon-11.
Tetrahedron Letters, 2003
A novel one-pot palladium-catalyzed cascade between 2-iodophenol, methyl bromomethylacrylate and ... more A novel one-pot palladium-catalyzed cascade between 2-iodophenol, methyl bromomethylacrylate and an arylboronic acid provides an efficient access to heterocycles possessing the 3,3-disubstituted-2,3-dihydrobenzofuran skeleton via allylation/carbopalladation/Suzuki cross-coupling.
Tetrahedron, 2007
Reactions. -(SZLOSEK-PINAUD, M.; DIAZ, P.; MARTINEZ, J.; LAMATY*, F.; Tetrahedron 63 (2007) 16, 3... more Reactions. -(SZLOSEK-PINAUD, M.; DIAZ, P.; MARTINEZ, J.; LAMATY*, F.; Tetrahedron 63 (2007) 16, 3340-3349; Lab. Amino-Acides Pept. Prot., Fac. Pharm.,
Phytochemistry, 1998
The seeds of Annona 9lauca have yielded four Annonaceous acetogenins. Two of them, glaucabellin a... more The seeds of Annona 9lauca have yielded four Annonaceous acetogenins. Two of them, glaucabellin and glaucaflorin, whose chemical structure was deduced by spectral and chemical methods, are new. ~'~
New Journal of Chemistry, 2000
... Magali Szlosek, Jean-François Peyrat, Christophe Chaboche, Xavier Franck, Reynald Hocquemille... more ... Magali Szlosek, Jean-François Peyrat, Christophe Chaboche, Xavier Franck, Reynald Hocquemiller and Bruno Figadère*. Laboratoire de Pharmacognosie [CNRS UPRES-A (BIOCIS)], Université de Paris-Sud ... 17, Since 1998: (a) SE Schaus, J. Branalt and EN Jacobsen, J. Org. ...
Molecules, 2013
The methyl transfer reaction from activated monomethyltin, via a modified Stille coupling reactio... more The methyl transfer reaction from activated monomethyltin, via a modified Stille coupling reaction, was studied under "ligandless" conditions on fully deprotected 5'-modified nucleosides and one dinucleotide. The reaction was optimized to proceed in a few minutes and quantitative yield, even under dilute conditions, thus affording a rapid and efficient new method for oligonucleotide labelling with carbon-11.
Journal of the American Chemical Society, 2001
The mycolactones were isolated in 1999 by Small and co-workers 1 from Mycobacterium ulcerans, the... more The mycolactones were isolated in 1999 by Small and co-workers 1 from Mycobacterium ulcerans, the causative pathogen of Buruli ulcer. This disease is characterized by the formation of large, painless, necrotic ulcers and the lack of an acute inflammatory response. Evidence from animal studies suggests that the mycolactones are directly responsible for the observed pathology, and they have attracted considerable attention for their highly potent apoptotic activity as well as for being the first examples of polyketide macrolides to be isolated from a human pathogen. The gross structure of these natural products was elucidated through 2D NMR experiments. 2 Via a combined approach employing both an NMR database and the preparation of model compounds, we recently established the relative and absolute configuration of the mycolactone core structure ( ). 3 Extending the newly developed universal NMR database concept in chiral solvents 4 to a proton NMR database, we report the complete structure of the mycolactones in this Communication.
The Journal of Organic Chemistry, 1998
ABSTRACT TMSOF 2-[(trimethylsilyl)oxy]furan has been used in an enantioselective aldol reaction f... more ABSTRACT TMSOF 2-[(trimethylsilyl)oxy]furan has been used in an enantioselective aldol reaction for the first time. Indeed, addition of TMSOF to achiral aldehydes, in the presence (R)-1,1‘-bi-2-naphthol (Binol), gave the corresponding butenolides with moderate diastereomeric ratios (dr = 60%) and ee's between 60 and 90%. Application of this reaction to the total synthesis of annonaceous muricatacin in only two steps (in regards to the numerous multistep syntheses published so far) illustrated the efficiency of this strategy.
European Journal of Organic Chemistry, 2013
This communication reports the simplified formation of methyl azide and its use in the Huisgen cy... more This communication reports the simplified formation of methyl azide and its use in the Huisgen cycloaddition for the rapid, efficient, and selective labeling of modified nucleosides and oligonucleotides. The transposition to radioactive
Current Medicinal Chemistry, 2008
Positron Emission Tomography has become a powerful scientific and clinical tool probing biochemic... more Positron Emission Tomography has become a powerful scientific and clinical tool probing biochemical processes in the human body. Their clinical applications have proven to be vital in the evaluation and diagnosis of diseases. This is due, in large part, to advances in instrumentation and synthetic chemistry. Carbon-11 is a valuable radionuclide in PET as it virtually permits the synthesis of radiolabelled versions of any compound of interest. The syntheses with carbon-11 present several features: limited number of labelled precursors, sub-micromolar amounts of the starting materials, and a need for the introduction of the radioisotope as late as possible in the synthesis. All of these reasons have restricted complex radiosyntheses. The short half-life of carbon-11 (20.4 min) requires the rapid preparation and purification of carbon-11 labelled molecules. Those have to be carried out immediately before use from cyclotron produced precursors ([ 11 C]CO2, [ 11 C]CO, [ 11 C]CH4) or reagents rapidly prepared from them ([ 11 C]CH3I, [ 11 C]COCl2, [ 11 C]HCN). As a consequence carbon-11 has been underused compared to fluorine-18. However, because of the increasing molecular complexity and diversity of biologically active compounds, there is a need for new methodologies giving access in short time and high yield to radioactive 11 C-probes. The aim of this review is to emphasize the methodologies used in this field and to give a comprehensive overview of the numerous advances, which occurred over the past decade. In addition, for each labelling technique or reaction reported, a special attention has been brought to classify the applications in function of the targeted medical domain.
ChemMedChem, 2014
A novel SiX-dipropargyl glycerol scaffold (X: H, F, or (18) F) was developed as a versatile prost... more A novel SiX-dipropargyl glycerol scaffold (X: H, F, or (18) F) was developed as a versatile prosthetic group that provides technical advantages for the preparation of dimeric radioligands based on silicon fluoride acceptor pre- or post-labeling with fluorine-18. Rapid conjugation with the prosthetic group takes place in microwave-assisted click conjugation under mild conditions. Thus, a bivalent homodimeric SiX-dipropargyl glycerol derivatized radioligand, [(18) F]BMPPSiF, with enhanced affinity was developed by using click conjugation. High uptake of the radioligand was demonstrated in 5-HT1A receptor-rich regions in the brain with positron emission tomography. Molecular docking studies (rigid protein-flexible ligand) of BMPPSiF and known antagonists (WAY-100635, MPPF, and MefWAY) with monomeric, dimeric, and multimeric 5-HT1A receptor models were performed, with the highest G score obtained for docked BMPPSiF: -6.766 as compared with all three antagonists on the monomeric model. Multimeric induced-fit docking was also performed to visualize the comparable mode of binding under in vivo conditions, and a notably improved G score of -8.455 was observed for BMPPSiF. These data directly correlate the high binding potential of BMPPSiF with the bivalent binding mode obtained in the biological studies. The present study warrants wide application of the SiX-dipropargyl glycerol prosthetic group in the development of ligands for imaging with enhanced affinity markers for specific targeting based on peptides, nucleosides, and lipids.
Chemistry - A European Journal, 2011
Positron emission tomography (PET) is a powerful molecular-imaging technique for physiological an... more Positron emission tomography (PET) is a powerful molecular-imaging technique for physiological and biological investigations in various areas, such as oncology, cardiology, and neurosciences, as well as for drug development. Due to
Bioorganic & Medicinal Chemistry Letters, 2003
Angewandte Chemie International Edition, 2000
ABSTRACT A stepwise addition of 2-trimethylsilyloxyfuran (2-TMSOF) to achiral aldehydes in the pr... more ABSTRACT A stepwise addition of 2-trimethylsilyloxyfuran (2-TMSOF) to achiral aldehydes in the presence of a chiral Lewis acid, such as a (R)-(1,1'-bi-2- naphthol)2Ti complex, affords the corresponding butenolides [Eq. (1)] in good yields with good to excellent ee values (70 to 96% ee). This is the first reported catalytic asymmetric autoinductive aldol reaction.