Synthesis of 3-phenylnaphthalenic derivatives as new selective MT2 melatoninergic ligands
2008; Elsevier BV; Volume: 16; Issue: 18 Linguagem: Inglês
10.1016/j.bmc.2008.08.052
ISSN1464-3391
AutoresSophie Poissonnier-Durieux, Mohamed Ettaoussi, Basile Pérès, Jean A. Boutin, Valérie Audinot, Caroline Bennejean, Philippe Delagrange, Daniel H. Caignard, Pierre Renard, Pascal Berthelot, Daniel Lesieur, Saı̈d Yous,
Tópico(s)Biochemical Acid Research Studies
ResumoA 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.
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