Synthesis of 3-phenylnaphthalenic derivatives as new selective MT₂ melatoninergic ligands

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• 作者：Sophie Poissonnier-Durieux ; Mohamed Ettaoussi ; Basile Pé ; rè ; s ; Jean A. Boutin ; Valé ; rie Audinot ; Caroline Bennejean ; Philippe Delagrange ; Daniel Henri Caignard ; Pierre Renard ; Pascal Berth
• 关键词：Melatonin ; MT₂ receptors ; 3-Phenylnaphthalene ; Selective antagonists
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2008
• 出版时间：15 September 2008
• 年：2008
• 卷：16
• 期：18
• 页码：8339-8348
• 全文大小：252 K

文摘

A series of naphthalenic analogues of melatonin were prepared and evaluated as melatonin receptor MT₂ selective ligands. Activity and MT₂ selectivity can be modulated with suitable variations of the C-3 phenyl and the acyl group on the C-1 side chain. Surprisingly, in contrast with what had been previously described in other series (2-benzylindoles, 2-benzylbenzofurans and 3-phenyltetralins), the presence of a C-3 phenyl with a functional group on the meta position seems to be primordial for MT₂ affinity and selectivity. Indeed, N-[2-(3-(3-hydroxymethylphenyl)-7-methoxynaphth-1-yl)ethyl]acetamide (21) is one of the best MT₂ selective ligands described until now and behaves as an antagonist.