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Bioorg Med Chem Lett. 2013 Jan 15;23(2):430-4. doi: 10.1016/j.bmcl.2012.11.069. Epub 2012 Nov 29.

Synthesis of new N-(arylcyclopropyl)acetamides and N-(arylvinyl)acetamides as conformationally-restricted ligands for melatonin receptors.

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Université de Paris-Sud, BIOCIS - UMR CNRS 8076, Faculté de Pharmacie, 5 rue J. B. Clément, 92296 Châtenay-Malabry, France.


N-(Arylcyclopropyl)acetamides and N-(arylvinyl)acetamides or methyl ureas have been prepared as constrained analogues of melatonin. The affinity of these new compounds for chicken brain melatonin receptors and recombinant human MT(1) and MT(2) receptors was evaluated using 2-[(125)I]-iodomelatonin as radioligand. Strict ethylenic or cyclopropyl analogues of the commercialized agonist agomelatine (Valdoxan®) were equipotent to agomelatine in binding bioassays. However, the ethylenic analogue was more effective than the cyclopropyl one in the melanophore aggregation bioassay, but was still less potent than the disubstituted 2,7-dimethoxy-naphtalenic compounds.

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