Synthesis of 3-phenylnaphthalenic derivatives as new selective MT(2) melatoninergic ligands.
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Poissonnier-Durieux S, Ettaoussi M, Peres B, Boutin JA, Audinot V, Bennejean C, Delagrange P, Caignard DH, Renard P, Berthelot P, Lesieur D, Yous S
Synthesis of 3-phenylnaphthalenic derivatives as new selective MT(2) melatoninergic ligands.
Bioorg Med Chem. 2008 Sep 15;16(18):8339-48. doi: 10.1016/j.bmc.2008.08.052. Epub 2008 Aug 27.
- PubMed ID
- 18778943 [ View in PubMed]
- Abstract
A series of naphthalenic analogues of melatonin were prepared and evaluated as melatonin receptor MT(2) selective ligands. Activity and MT(2) 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 MT(2) affinity and selectivity. Indeed, N-[2-(3-(3-hydroxymethylphenyl)-7-methoxynaphth-1-yl)ethyl]acetamide (21) is one of the best MT(2) selective ligands described until now and behaves as an antagonist.
DrugBank Data that Cites this Article
- Binding Properties
Drug Target Property Measurement pH Temperature (°C) Agomelatine Melatonin receptor type 1A Ki (nM) 0.06 N/A N/A Details Agomelatine Melatonin receptor type 1B EC 50 (nM) 0.1 N/A N/A Details Agomelatine Melatonin receptor type 1B Ki (nM) 0.27 N/A N/A Details Melatonin Melatonin receptor type 1A Ki (nM) 0.14 N/A N/A Details Melatonin Melatonin receptor type 1B EC 50 (nM) 0.49 N/A N/A Details Melatonin Melatonin receptor type 1B Ki (nM) 0.41 N/A N/A Details