Design and synthesis of benzofuranic derivatives as new ligands at the melatonin-binding site MT3

Mohamed Ettaoussi; Basile Péres; Fréderique Klupsch; Philippe Delagrange; Jean-A Boutin; Pierre Renard; Daniel-H Caignard; Philippe Chavatte; Pascal Berthelot; Daniel Lesieur; Saïd Yous

doi:10.1016/j.bmc.2008.03.036

Design and synthesis of benzofuranic derivatives as new ligands at the melatonin-binding site MT3

Bioorg Med Chem. 2008 May 1;16(9):4954-62. doi: 10.1016/j.bmc.2008.03.036. Epub 2008 Mar 17.

Authors

Mohamed Ettaoussi¹, Basile Péres, Fréderique Klupsch, Philippe Delagrange, Jean-A Boutin, Pierre Renard, Daniel-H Caignard, Philippe Chavatte, Pascal Berthelot, Daniel Lesieur, Saïd Yous

Affiliation

¹ Laboratoire de Chimie Thérapeutique (EA 1043), Faculté des Sciences Pharmaceutiques et Biologiques, Université de Lille, 3, rue du professeur Laguesse, 2, BP 83, 59006 Lille Cedex, France.

PMID: 18372181
DOI: 10.1016/j.bmc.2008.03.036

Abstract

Benzofuranic analogues of MCA-NAT (5-methoxycarbonylamino-N-acetyltryptamine) have been synthesized and evaluated as melatonin receptor ligands. Introduction of a methoxycarbonylamino substituent in the C-5 position of the benzofurane nucleus obtains MT(3) selective ligands. This selectivity can be modulated with suitable variations of the C-5 position and the acyl group on the C-3 side chain.

MeSH terms

Binding Sites
Dose-Response Relationship, Drug
Drug Design*
Inhibitory Concentration 50
Ligands
Melatonin / chemistry*
Molecular Structure
Receptors, Melatonin / drug effects*
Stereoisomerism
Structure-Activity Relationship
Tryptamines / chemical synthesis*
Tryptamines / chemistry
Tryptamines / pharmacology*

Substances

5-methoxycarbonylamino-N-acetyltryptamine
Ligands
Receptors, Melatonin
Tryptamines
Melatonin