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Paper | Regular issue | Vol 60, No. 12, 2003, pp.2621-2630
Published online, 2nd October, 2003
DOI: 10.3987/COM-03-9859
Synthesis of 2(3H)-Benzoxazolone Derivatives as Potential Melatonin Receptor Ligands

Christophe Mésangeau, Jacques H. Poupaert, Pascal Carato,* and Saïd Yous

*Laboratoire de Chimie Thérapeutique, Faculté des Sciences Pharmaceutiques et Biologiques de Lille, Université de Lille 2, 3, rue du Professeur Laguesse, BP 83, F-59006 Lille, France

Abstract

This article reports the synthesis of new 2(3H)-benzoxazolone-based ligands for the melatonin receptors in which an acetamidopropyl side-chain was incorporated. Construction of the acetamidopropyl moiety was achieved via a Wadsworth-Emmons approach. Although these compounds can be seen as derivatives of N-[3-(3-methoxyphenyl)propyl]acetamide (MPPA), which is the exact analogue of melatonin in which the 1,2-indole nitrogen atoms are deleted, they exhibit lower affinities for the melatonin receptors probably due to an unfavourable steric bulk and hydrophilic interactions