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Design and Synthesis of New Naphthalenic Derivatives as Ligands for 2-[125I]Iodomelaton Binding Site

Design and Synthesis of New Naphthalenic Derivatives as Ligands for 2-[125I]Iodomelaton Binding Site

  1. trptamene
    New melatonin-like agents were designed from the frameworks of 2,5-dimethoxyphenethylamine,
    an important structural moiety for the 5-HT receptor, and (2-methoxynaphthy1)-
    ethylamine. The compounds were synthesized by classical methods and evaluated in binding
    assays with chicken brain membranes using 2-[1251]iodomelatonin as the radioligand. Preliminary
    studies on the series of N-acyl-disubstituted phenethylamines showed the favorable
    role of the methoxy group in the ortho position of the side chain on the affinity for the receptor
    (K, = 8 f 0.2 nM) for N-[2-(2-methoxy-5-bromophenyl)ethyllpropionamid(e3 0). This effect
    was confirmed in a series of the naphthalene derivatives, a bioisosteric moiety of the indole
    ring, and several potent ligands for melatonin binding sites were prepared such as N-1242-
    methoxynaphthyl)ethyllpropionamide (4b) (Ki = 0.67 f 0.05 nM) and N-[2-(2,7-dimethoxynaphthyl)
    ethyllcyclopropylformamide (K, = 0.05 f 0.004 nM) (4k). Structure-activity relationships
    are discussed with regard to melatonin and bioisosteric naphthalenic compound 2. The
    Ki value for 4b was affected to a similar extent to that of melatonin by GTP-y-S or Mn2+ in
    competition experiments, suggesting an agonist profile for this compound.

    J. Med. Chem. 1995,38, 2050-2060