PMID: 7932550Sep 30, 1994Paper

Synthesis and structure-activity relationships of novel naphthalenic and bioisosteric related amidic derivatives as melatonin receptor ligands

Journal of Medicinal Chemistry
P DepreuxB Guardiola


A series of N-naphthylethyl amide derivatives were synthesized and evaluated as melatonin receptor ligands. The affinity of each compound for the melatonin receptor was determined by binding studies using [2-125I]iodomelatonin on ovine pars tuberalis membrane homogenates. Structure-activity relationships led to the conclusion that naphthalene is a bioisostere of the indole moiety of melatonin. Moreover it appears that the affinity is strongly affected by the size of the substituent of the nitrogen of the amidic function. Many of these ligands give biphasic dose-response curves which suggests that there may be two melatonin receptor subtypes within the ovine pars tuberalis cells. The replacement of naphthalene by benzofuran or benzothiophene did not strongly alter the affinity for the melatonin receptor. In contrast, the benzimidazole analogue was a poor ligand. Compound 7, the naphthalenic analogue of melatonin, a selective ligand of the melatonin receptor and an agonist derivative, has been selected for clinical development.


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Jun 10, 1998·Biology of the Cell·D SugdenP J Garratt
Jan 5, 1999·Bioorganic & Medicinal Chemistry Letters·S KloubertM Langlois
Mar 21, 1998·Bioorganic & Medicinal Chemistry·E FourmaintrauxH E Howell
Feb 5, 2000·Bioorganic & Medicinal Chemistry·M Mathé-AllainmatM Langlois
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Jan 14, 2004·European Journal of Biochemistry·Gilles FerryJean A Boutin
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Wen-Bin WeiHai-Bo Wang
May 11, 2006·The Australian and New Zealand Journal of Psychiatry·Trevor R Norman
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Feb 5, 2002·Chemical & Pharmaceutical Bulletin·Andrew TsotinisDavid Sugden
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Apr 4, 2008·Biochemical Pharmacology·Valérie AudinotJean A Boutin
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Oct 15, 2013·British Journal of Pharmacology·Céline LegrosOlivier Nosjean
Apr 29, 1998·Annals of Medicine·T Kokkola, J T Laitinen
Sep 16, 2011·Expert Opinion on Pharmacotherapy·Regina M Carney, Richard C Shelton
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