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