New ligands of the ghrelin receptor based on the 1,2,4-triazole scaffold by introduction of a second chiral center

Mathieu Maingot; Anne-Laure Blayo; Severine Denoyelle; Céline M’kadmi; Marjorie Damian; Sophie Mary; Didier Gagne; Pierre Sanchez; Babette Aicher; Peter Schmidt; Gilbert Müller; Michael Teifel; Eckhard Günther; Jacky Marie; Jean-Louis Banères; Jean Martinez; Jean-Alain Fehrentz

doi:10.1016/j.bmcl.2016.04.003

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New ligands of the ghrelin receptor based on the 1,2,4-triazole scaffold by introduction of a second chiral center

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New ligands of the ghrelin receptor based on the 1,2,4-triazole scaffold by introduction of a second chiral center

Mathieu Maingot, Anne-Laure Blayo, Severine Denoyelle, Céline M’kadmi, Marjorie Damian, Sophie Mary, Didier Gagne, Pierre Sanchez, Babette Aicher, Peter Schmidt, …

Bioorganic and Medicinal Chemistry Letters, Vol.26(10), pp.2408-2412

05/2016

DOI: https://doi.org/10.1016/j.bmcl.2016.04.003

PMID: 27072910

Abstract

Antagonist

Chirality

Ghrelin receptor (GHS-R1a)

Inverse agonist

Structural modulation

1 2 4-Triazole scaffold

Introducing a second chiral center on our previously described 1,2,4-triazole, allowed us to increase diversity and elongate the 'C-terminal part' of the molecule. Therefore, we were able to explore mimics of the substance P analogs described as inverse agonists. Some compounds presented affinities in the nanomolar range and potent biological activities, while one exhibited a partial inverse agonist behavior similar to a Substance P analog.

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Title: New ligands of the ghrelin receptor based on the 1,2,4-triazole scaffold by introduction of a second chiral center
Creators - without role: Mathieu Maingot - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Anne-Laure Blayo - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Severine Denoyelle - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Céline M’kadmi - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Marjorie Damian - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Sophie Mary - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Didier Gagne - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Pierre Sanchez - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Babette Aicher - Aeterna Zentaris
Peter Schmidt - Aeterna Zentaris
Gilbert Müller - Aeterna Zentaris
Michael Teifel - Aeterna Zentaris
Eckhard Günther - Aeterna Zentaris
Jacky Marie - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Jean-Louis Banères - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Jean Martinez - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Jean-Alain Fehrentz - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Publication Details: Bioorganic and Medicinal Chemistry Letters, Vol.26(10), pp.2408-2412
Identifiers: 9946657709311
Academic Unit: Institut des Biomolécules Max Mousseron - IBMM
Language: English
Resource Type: Journal article
Local Fields: hal-02871896