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

Silvia Rivara, Federica Vacondio, Alessandro Fioni, Claudia Silva, Caterina Carmi, Marco Mor, Valeria Lucini, Marilou Pannacci, Alessia Caronno, Francesco Scaglione, Gabriella Gobbi, Gilberto Spadoni, Annalida Bedini, Pierfrancesco Orlando, Simone Lucarini, Giorgio Tarzia

Research output: Contribution to journalArticle

Abstract

(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.

Original languageEnglish
Pages (from-to)1746-1755
Number of pages10
JournalChemMedChem
Volume4
Issue number10
DOIs
Publication statusPublished - 2009

Keywords

  • Biotransformations
  • Drug design
  • Melatonin
  • Metabolism
  • Receptors

ASJC Scopus subject areas

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry
  • Molecular Medicine

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  • Cite this

    Rivara, S., Vacondio, F., Fioni, A., Silva, C., Carmi, C., Mor, M., Lucini, V., Pannacci, M., Caronno, A., Scaglione, F., Gobbi, G., Spadoni, G., Bedini, A., Orlando, P., Lucarini, S., & Tarzia, G. (2009). N-(anilinoethyl)amides: Design and synthesis of metabolically stable, selective melatonin receptor ligands. ChemMedChem, 4(10), 1746-1755. https://doi.org/10.1002/cmdc.200900240