André Mann - Academia.edu (original) (raw)
Papers by André Mann
ChemInform, 2010
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
L Actualite Chimique, 2003
Dopamine is a major neurotransmitter in the brain. In combining molecular biology and medicinal c... more Dopamine is a major neurotransmitter in the brain. In combining molecular biology and medicinal chemistry it was possible to identify 5 sub-types of the dopaminergic receptor (D 1 ...D 5 ). A lead-optimisation strategy applied to the neuroleptic drug sulpiride, provided two potent and selective ligands for the D 3 receptor (nafadotride and BP 897). As the implication of the D 3 receptor in schizophrenia, Parkinson's disease and drug addiction has been postulated, BP 897 seems an ideal drug candidate to evaluate the function of the D 3 receptors in man.
ChemInform, 2011
A variety of substituted piperidines and 1,4‐substituted indolizine (XVII) are prepared using the... more A variety of substituted piperidines and 1,4‐substituted indolizine (XVII) are prepared using the indium‐mediated aminoallylation and ‐crotylation of aldehydes with 1‐amino‐2‐indanol (I), Rh(I)‐catalyzed hydroformylative cyclohydrocarbonylation, opening of the oxazolidines with Grignard reagents and removal of the chiral auxiliaries.
Tetrahedron Letters, 1987
Tetrahedron Letters, 1993
Allylsilanes preapared from a-aminoacids react with acyl chlorides in the presence of TiC14 to gi... more Allylsilanes preapared from a-aminoacids react with acyl chlorides in the presence of TiC14 to give unsaturated amino ketones, easily tranqformed into pyrrolidine derivatives, whereas addition to al&hydes gave 2,tSdisubstituted tetrahydropyridines.
The Journal of Organic Chemistry, 2012
The Journal of Organic Chemistry, 1996
... c) MeC CLi, THF, −78 °C, (89%); (d) K-Selectride, THF, −100 °C (72%); (e) BuLi, LiBr, TosCl, ... more ... c) MeC CLi, THF, −78 °C, (89%); (d) K-Selectride, THF, −100 °C (72%); (e) BuLi, LiBr, TosCl, THF, then CuBr·DMS, LiBr, −60 °C (75%: 5 and epi-5); (f) MeCuCNLi, THF, −78 °C (76% of 3 and 4% of epi-3); (g) Cp 2 ... First Enantiocontrolled Formal Synthesis of (+)-Neovibsanin B, A ...
European Journal of Pharmacology: Molecular Pharmacology, 1990
Substituent variations on th~ pyrrolidinyl nitrogen of sulphide, a selective D 2 dopamine antagon... more Substituent variations on th~ pyrrolidinyl nitrogen of sulphide, a selective D 2 dopamine antagonist, showed that in vitro and in vivo activities are concentrated in the (S) optical series for N-alkyl analogs and in the (R) series for N-benzyl analogs. To account for these unusual structure-activi D, relationships, a pharmacophoric model was built from the crystallographic structure of (-)piquindone and extended to 14 other D 2 antagonists. This model considers the lone pair orientation of the basic nitrogen rather than its spatial location. Two distinct active conformations for benzamides were defined, corresponding to the (S) and (R) series. An extended pharmacophore is then propo~d involving four main anchoring areas: (i) an aromatic site Ar h (ii) a tertiary nitrogen with its lone pair orthogonal to the Ar 1 plane, ('ni) a dipole A1 coplanar to the Ar 1 ring and (iv) three sites for the N-substituent, including a small hydrophobie pocket and two differen~ aromatic binding sites Ar 2 and Ar~. To probe the predictive value of this model, structures were designed and several compounds were synthesized and tested as inhibitors of [Jzsf]iodosulpride binding to rat striatal membranes and as antagonists of apomorphine-induced stereotyped behavior in lrfice.
Clinical Neuropharmacology, 1995
Scientific reports, Jan 24, 2016
Hedgehog (Hh) is a critical regulator of adipogenesis. Extracellular vesicles are natural Hh carr... more Hedgehog (Hh) is a critical regulator of adipogenesis. Extracellular vesicles are natural Hh carriers, as illustrated by activated/apoptotic lymphocytes specifically shedding microparticles (MP) bearing the morphogen (MP(Hh+)). We show that MP(Hh+) inhibit adipocyte differentiation and orientate mesenchymal stem cells towards a pro-osteogenic program. Despite a Smoothened (Smo)-dependency, MP(Hh+) anti-adipogenic effects do not activate a canonical Hh signalling pathway in contrast to those elicited either by the Smo agonist SAG or recombinant Sonic Hedgehog. The Smo agonist GSA-10 recapitulates many of the hallmarks of MP(Hh+) anti-adipogenic effects. The adipogenesis blockade induced by MP(Hh+) and GSA-10 was abolished by the Smo antagonist LDE225. We further elucidate a Smo/Lkb1/Ampk axis as the non-canonical Hh pathway used by MP(Hh+) and GSA-10 to inhibit adipocyte differentiation. Our results highlight for the first time the ability of Hh-enriched MP to signal via a non-canoni...
ACS Chemical Biology, 2015
G protein-coupled receptors (GPCRs) have been described to form hetero-oligomers. The importance ... more G protein-coupled receptors (GPCRs) have been described to form hetero-oligomers. The importance of these complexes in physiology and pathology is considered crucial, and hetero-dimers represent promising new targets to discover innovative therapeutics. However, there is a lack of binding assays to allow the evaluation of ligand affinity for GPCR hetero-oligomers. Using dopamine receptors and more specifically the D 1 and D 3 receptors as GPCR models, we developed a new time-resolved FRET (TR-FRET) based assay to determine ligand affinity for the D 1 /D 3 heteromer. Based on the high-resolution structure of the dopamine D 3 receptor (D 3 R), six fluorescent probes derived from a known D 3 R partial agonist (BP 897) were designed, synthesized and evaluated as high affinity and selective ligands for the D 3 /D 2 receptors, and for other dopamine receptor subtypes. The highest affinity ligand 21 was then employed in the development of the D 1 /D 3 heteromer assay. The TR-FRET was monitored between a fluorescent tag donor carried by the D 1 receptor (D 1 R) and a fluorescent acceptor D 3 R ligand 21. The newly reported assay, easy to implement on other G protein-coupled receptors, constitutes an attractive strategy to screen for heteromer ligands.
Tetrahedron Letters, 2003
Scheme 2 and the legend below must be corrected as follows: Reference 12 must be corrected as fol... more Scheme 2 and the legend below must be corrected as follows: Reference 12 must be corrected as follows: 12. The Merrifield support was purchased from Novabiochem 1% DVB, 200-400 mesh, 1-1.5 mmol/g. When the procedure reported under Scheme 2 was used, the loading of resin B was shown to be three times higher than the corresponding loading obtained by Tietze's procedure. 11 Scheme 2. Reagents and conditions: (i) NaH, DMF, 80°C; (ii) pTsOH, MeOH/CH 2 Cl 2 ; (iii) diketene, DMAP, CH 2 Cl 2 , −50°C to rt; (iv) HC(OMe) 3 , H 2 SO 4 (cat.), rt, then heating at 60°C; (v) a. LDA, THF, −78°C, b. DMPU, c. tBuMe 2 SiCl, −78°C, then rt.
Synthetic Communications, 1989
ZnBr2 in dichloromethane is a convenient reagent for mild and selective removal of the tert-butox... more ZnBr2 in dichloromethane is a convenient reagent for mild and selective removal of the tert-butoxycarbonyl group from secondary amines.
Synthesis, 2010
... New York. Microwave-Assisted Domino Hydroformylation/Cyclization Reactions: Scope and Limitat... more ... New York. Microwave-Assisted Domino Hydroformylation/Cyclization Reactions: Scope and Limitations. Etienne Airiau a , Claire Chemin a , Nicolas Girard a , Giacomo Lonzi b , André Mann* a , Elena Petricci b , Jessica Salvadori b , Maurizio Taddei* b. ...
Journal of Labelled Compounds and Radiopharmaceuticals, 1987
The preparation of the tritium labelled benzamides, S‐[3H]‐DO‐710 and S‐[3H]‐azidosulpride is rep... more The preparation of the tritium labelled benzamides, S‐[3H]‐DO‐710 and S‐[3H]‐azidosulpride is reported. The synthesis involves enantioselective preparation of the pyrrolidinyl moiety, reductive tritiation of an allylic precursor and conversion of an amino, to an azido function.Both labelled ligands are D2‐dopaminergic antagonists, useful in binding experiments and to achieve covalent bonds after light exposure at the receptor site level.
British Journal of Pharmacology, 1977
1 (t‐Butyl‐amino‐3‐ol‐2‐propyl) oximino‐9 fluorene is a new β2‐adrenoceptor blocking agent with a... more 1 (t‐Butyl‐amino‐3‐ol‐2‐propyl) oximino‐9 fluorene is a new β2‐adrenoceptor blocking agent with a pA2 of 9.23 ± 0.25 on isolated trachea.2 It provokes hypertension in normotensive rats and does not prevent arterial hypertension in SHR rats, although it does prevent the renin secretion normally induced by isoprenaline infusion.
ChemInform, 2010
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
L Actualite Chimique, 2003
Dopamine is a major neurotransmitter in the brain. In combining molecular biology and medicinal c... more Dopamine is a major neurotransmitter in the brain. In combining molecular biology and medicinal chemistry it was possible to identify 5 sub-types of the dopaminergic receptor (D 1 ...D 5 ). A lead-optimisation strategy applied to the neuroleptic drug sulpiride, provided two potent and selective ligands for the D 3 receptor (nafadotride and BP 897). As the implication of the D 3 receptor in schizophrenia, Parkinson's disease and drug addiction has been postulated, BP 897 seems an ideal drug candidate to evaluate the function of the D 3 receptors in man.
ChemInform, 2011
A variety of substituted piperidines and 1,4‐substituted indolizine (XVII) are prepared using the... more A variety of substituted piperidines and 1,4‐substituted indolizine (XVII) are prepared using the indium‐mediated aminoallylation and ‐crotylation of aldehydes with 1‐amino‐2‐indanol (I), Rh(I)‐catalyzed hydroformylative cyclohydrocarbonylation, opening of the oxazolidines with Grignard reagents and removal of the chiral auxiliaries.
Tetrahedron Letters, 1987
Tetrahedron Letters, 1993
Allylsilanes preapared from a-aminoacids react with acyl chlorides in the presence of TiC14 to gi... more Allylsilanes preapared from a-aminoacids react with acyl chlorides in the presence of TiC14 to give unsaturated amino ketones, easily tranqformed into pyrrolidine derivatives, whereas addition to al&hydes gave 2,tSdisubstituted tetrahydropyridines.
The Journal of Organic Chemistry, 2012
The Journal of Organic Chemistry, 1996
... c) MeC CLi, THF, −78 °C, (89%); (d) K-Selectride, THF, −100 °C (72%); (e) BuLi, LiBr, TosCl, ... more ... c) MeC CLi, THF, −78 °C, (89%); (d) K-Selectride, THF, −100 °C (72%); (e) BuLi, LiBr, TosCl, THF, then CuBr·DMS, LiBr, −60 °C (75%: 5 and epi-5); (f) MeCuCNLi, THF, −78 °C (76% of 3 and 4% of epi-3); (g) Cp 2 ... First Enantiocontrolled Formal Synthesis of (+)-Neovibsanin B, A ...
European Journal of Pharmacology: Molecular Pharmacology, 1990
Substituent variations on th~ pyrrolidinyl nitrogen of sulphide, a selective D 2 dopamine antagon... more Substituent variations on th~ pyrrolidinyl nitrogen of sulphide, a selective D 2 dopamine antagonist, showed that in vitro and in vivo activities are concentrated in the (S) optical series for N-alkyl analogs and in the (R) series for N-benzyl analogs. To account for these unusual structure-activi D, relationships, a pharmacophoric model was built from the crystallographic structure of (-)piquindone and extended to 14 other D 2 antagonists. This model considers the lone pair orientation of the basic nitrogen rather than its spatial location. Two distinct active conformations for benzamides were defined, corresponding to the (S) and (R) series. An extended pharmacophore is then propo~d involving four main anchoring areas: (i) an aromatic site Ar h (ii) a tertiary nitrogen with its lone pair orthogonal to the Ar 1 plane, ('ni) a dipole A1 coplanar to the Ar 1 ring and (iv) three sites for the N-substituent, including a small hydrophobie pocket and two differen~ aromatic binding sites Ar 2 and Ar~. To probe the predictive value of this model, structures were designed and several compounds were synthesized and tested as inhibitors of [Jzsf]iodosulpride binding to rat striatal membranes and as antagonists of apomorphine-induced stereotyped behavior in lrfice.
Clinical Neuropharmacology, 1995
Scientific reports, Jan 24, 2016
Hedgehog (Hh) is a critical regulator of adipogenesis. Extracellular vesicles are natural Hh carr... more Hedgehog (Hh) is a critical regulator of adipogenesis. Extracellular vesicles are natural Hh carriers, as illustrated by activated/apoptotic lymphocytes specifically shedding microparticles (MP) bearing the morphogen (MP(Hh+)). We show that MP(Hh+) inhibit adipocyte differentiation and orientate mesenchymal stem cells towards a pro-osteogenic program. Despite a Smoothened (Smo)-dependency, MP(Hh+) anti-adipogenic effects do not activate a canonical Hh signalling pathway in contrast to those elicited either by the Smo agonist SAG or recombinant Sonic Hedgehog. The Smo agonist GSA-10 recapitulates many of the hallmarks of MP(Hh+) anti-adipogenic effects. The adipogenesis blockade induced by MP(Hh+) and GSA-10 was abolished by the Smo antagonist LDE225. We further elucidate a Smo/Lkb1/Ampk axis as the non-canonical Hh pathway used by MP(Hh+) and GSA-10 to inhibit adipocyte differentiation. Our results highlight for the first time the ability of Hh-enriched MP to signal via a non-canoni...
ACS Chemical Biology, 2015
G protein-coupled receptors (GPCRs) have been described to form hetero-oligomers. The importance ... more G protein-coupled receptors (GPCRs) have been described to form hetero-oligomers. The importance of these complexes in physiology and pathology is considered crucial, and hetero-dimers represent promising new targets to discover innovative therapeutics. However, there is a lack of binding assays to allow the evaluation of ligand affinity for GPCR hetero-oligomers. Using dopamine receptors and more specifically the D 1 and D 3 receptors as GPCR models, we developed a new time-resolved FRET (TR-FRET) based assay to determine ligand affinity for the D 1 /D 3 heteromer. Based on the high-resolution structure of the dopamine D 3 receptor (D 3 R), six fluorescent probes derived from a known D 3 R partial agonist (BP 897) were designed, synthesized and evaluated as high affinity and selective ligands for the D 3 /D 2 receptors, and for other dopamine receptor subtypes. The highest affinity ligand 21 was then employed in the development of the D 1 /D 3 heteromer assay. The TR-FRET was monitored between a fluorescent tag donor carried by the D 1 receptor (D 1 R) and a fluorescent acceptor D 3 R ligand 21. The newly reported assay, easy to implement on other G protein-coupled receptors, constitutes an attractive strategy to screen for heteromer ligands.
Tetrahedron Letters, 2003
Scheme 2 and the legend below must be corrected as follows: Reference 12 must be corrected as fol... more Scheme 2 and the legend below must be corrected as follows: Reference 12 must be corrected as follows: 12. The Merrifield support was purchased from Novabiochem 1% DVB, 200-400 mesh, 1-1.5 mmol/g. When the procedure reported under Scheme 2 was used, the loading of resin B was shown to be three times higher than the corresponding loading obtained by Tietze's procedure. 11 Scheme 2. Reagents and conditions: (i) NaH, DMF, 80°C; (ii) pTsOH, MeOH/CH 2 Cl 2 ; (iii) diketene, DMAP, CH 2 Cl 2 , −50°C to rt; (iv) HC(OMe) 3 , H 2 SO 4 (cat.), rt, then heating at 60°C; (v) a. LDA, THF, −78°C, b. DMPU, c. tBuMe 2 SiCl, −78°C, then rt.
Synthetic Communications, 1989
ZnBr2 in dichloromethane is a convenient reagent for mild and selective removal of the tert-butox... more ZnBr2 in dichloromethane is a convenient reagent for mild and selective removal of the tert-butoxycarbonyl group from secondary amines.
Synthesis, 2010
... New York. Microwave-Assisted Domino Hydroformylation/Cyclization Reactions: Scope and Limitat... more ... New York. Microwave-Assisted Domino Hydroformylation/Cyclization Reactions: Scope and Limitations. Etienne Airiau a , Claire Chemin a , Nicolas Girard a , Giacomo Lonzi b , André Mann* a , Elena Petricci b , Jessica Salvadori b , Maurizio Taddei* b. ...
Journal of Labelled Compounds and Radiopharmaceuticals, 1987
The preparation of the tritium labelled benzamides, S‐[3H]‐DO‐710 and S‐[3H]‐azidosulpride is rep... more The preparation of the tritium labelled benzamides, S‐[3H]‐DO‐710 and S‐[3H]‐azidosulpride is reported. The synthesis involves enantioselective preparation of the pyrrolidinyl moiety, reductive tritiation of an allylic precursor and conversion of an amino, to an azido function.Both labelled ligands are D2‐dopaminergic antagonists, useful in binding experiments and to achieve covalent bonds after light exposure at the receptor site level.
British Journal of Pharmacology, 1977
1 (t‐Butyl‐amino‐3‐ol‐2‐propyl) oximino‐9 fluorene is a new β2‐adrenoceptor blocking agent with a... more 1 (t‐Butyl‐amino‐3‐ol‐2‐propyl) oximino‐9 fluorene is a new β2‐adrenoceptor blocking agent with a pA2 of 9.23 ± 0.25 on isolated trachea.2 It provokes hypertension in normotensive rats and does not prevent arterial hypertension in SHR rats, although it does prevent the renin secretion normally induced by isoprenaline infusion.