Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors.

Alessia Carocci, Alessia Catalano, Angelo Lovece, Giovanni Lentini, Andrea Duranti, Valeria Lucini, Marilou Pannacci, Francesco Scaglione, Carlo Franchini

Dipartimento Farmaco-Chimico, Università degli Studi di Bari, Via E. Orabona 4, 70126 Bari, Italy. carocci@farmchim.uniba.it

Bioorganic & medicinal chemistry 2010 Sep 1

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A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT(1) and MT(2) receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists. Copyright 2010 Elsevier Ltd. All rights reserved.

Citation

Alessia Carocci, Alessia Catalano, Angelo Lovece, Giovanni Lentini, Andrea Duranti, Valeria Lucini, Marilou Pannacci, Francesco Scaglione, Carlo Franchini. Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorganic & medicinal chemistry. 2010 Sep 1;18(17):6496-511