N-(Anilinoethyl)amides: design and synthesis of metabolically stable, selective melatonin receptor ligands

(Chemical Equation Presented) Analysis of in vitro metabolites of the melatonin ligand UCM765 allowed the identification of structural elements responsible for its metabolic liability. Analytical techniques, SAR studies, chemical synthesis, and binding experiments enabled the discovery of a new high-affinity MT2-selective melatonin partial agonist endowed with a binding profile similar to that of the parent compound and with improved stability to oxidative metabolism.