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J. A. Fehrentz,
L. Demange,
A. Moulin, D. Boeglin,
D. Mousseaux,
J. Ryan,
J. C. Galleyrand,
D. Gagne,
G. Berge,
C. Goze,
C. M'Kadmi,
D. Perrissoud,
V. Locatelli,
J. Martinez
Journal of Peptide Science. 01/2006; 12:211-211.
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ABSTRACT: A new and easy protocol for the formation of substituted 4,5-dihydro-1,2,4-triazin-6(1H)-ones was developed on solid support. The heterocyclic compounds were formed by nucleophilic reaction of hydrazine on thioamide esters. As cyclization was concomitant with cleavage from the support, substituted 4,5-dihydrotriazinones were obtained in high purity. (C) 2002 Elsevier Science Ltd. All rights reserved.
Tetrahedron Letters. 01/2003; 44(3):459-462.
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ABSTRACT: A straightforward synthesis of 2,6-disubstituted piperidines bearing alpha-amino acid side-chains was developed. Synthesis was based on a Homer-Wadsworth-Emmons condensation of a beta-ketophosphonate derived from an alpha-amino acid residue with a beta-homologated aldehyde of an N-protected amino acid residue. The generated alpha-beta unsaturated ketones were then reduced, deprotected, and cyclized in a hydrogenation/hydrogenolysis one-pot procedure to yield piperid-me moieties. Introduction of a new conformational restriction in the obtained molecules allowed total assignment of the stereocenters by NMR experiments. This assignment allowed us to propose a mechanistic pathway during the cyclization process, explaining the loss of exocyclic carbon-center configuration. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
European Journal of Organic Chemistry. 01/2003;
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ABSTRACT: Anchoring of an alpha-amino-acid amide residue by its amine function to a carbamate resin followed by primary amide Hofmann rearrangement led to a gem-diamino residue linked to the resin. The generated primary amine could be acylated with various carboxylic compounds offering a large variety of molecules. Furthermore, this new solid-phase strategy allowed a reliable synthesis of a gem-diamino monomeric residue which could not be easily obtained in solution due to the limited stability of monocarbamate-protected gem-diaminoalkyl derivatives. (C) 2003 Elsevier Science Ltd. All rights reserved.
Tetrahedron Letters. 01/2003; 44(25):4797-4799.
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F Broglio,
F Boutignon,
A Benso,
C Gottero,
F Prodam,
E Arvat,
C Ghè,
F Catapano,
A Torsello,
V Locatelli,
G Muccioli, D Boeglin,
V Guerlavais,
J A Fehrentz,
J Martinez,
E Ghigo,
R Deghenghi
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ABSTRACT: EP1572 UMV1843 [Aib-DTrp-DgTrp-CHO]) is a new peptido-mimetic GH secretagogue (GHS) showing binding potency to the GHS-receptor in animal and human tissues similar to that of ghrelin and peptidyl GHS. EP1572 induces marked GH increase after s.c. administration in neonatal rats. Preliminary data in 2 normal young men show that: 1) acute i.v. EP1572 administration (1.0 microg/kg) induces strong and selective increase of GH levels; 2) single oral EP1572 administration strongly and reproducibly increases GH levels even after a dose as low as 0.06 mg/kg. Thus, EP1572 is a new peptido-mimetic GHS with potent and selective GH-releasing activity.
Journal of endocrinological investigation 10/2002; 25(8):RC26-8. · 1.57 Impact Factor
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ABSTRACT: Starting from EP 51389, a potent growth hormone secretagogue (GHS), a new series of GHS has been designed, synthesized and tested. This series was built on a gem-diamino moiety and a structure activity relationship study was performed including N-methylation of the amide bonds. Some analogues exhibited more powerful activity than Hexarelin, they were active per os on dog and have been selected as candidates for further development.
Letters in Peptide Science 01/2001; 8(3-5):187-193.
