Synthesis of 2(3H)-benzoxazolone derivatives as potential melatonin receptor ligands.     Mesangeau, Christophe; Poupaert, Jacques H.; Carato, Pascal; Yous, Said.    Laboratoire de Chimie Therapeutique, Faculte des Sciences Pharmaceutiques et Biologiques de Lille,  Lille,  Fr.    Heterocycles  (2003),  60(12),  2621-2630.  CODEN: HTCYAM  ISSN: 0385-5414.  Journal  written in English.    CAN 140:163742    AN 2003:975859    CAPLUS  

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, e.g., I.  Construction of the acetamidopropyl moiety was achieved via a Wadsworth-Emmons approach.  Although these compds. can be seen as derivs. of N-[3-(3-methoxyphenyl)propyl]acetamide (MPPA; II), which is the exact analog of melatonin in which the 1,2-indole nitrogen atoms are deleted, they exhibit lower affinities for the melatonin receptors probably due to an unfavorable steric bulk and hydrophilic interactions.  
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Indexing -- Section 28-6  (Heterocyclic Compounds (More Than One Hetero Atom)  
Section cross-reference(s): 1