title: Design and synthesis of 2-phenylimidazo[1,2-a]pyridines as a novel class of melatonin receptor ligands.
abstract: A novel class of imidazo[1,2-a]pyridines as melatonin receptor ligands is designed and synthesized. The affinities of 3-(6-methoxy-2-phenylimidazo[1,2-a]pyridine-3-yl)-N-methyl-propionamide 8, N-[2-(6-methoxy-2-phenylimidazo[1,2-a]pyridine-3-yl)-ethyl]-acetamide 13 and N-(1-hydroxy-3-(5-methoxy-2-phenyl-1H-indol-3-yl)propan-2-yl)acetamide 18 are evaluated for binding on melatonin receptors. Compound 8 present good selectivity for MT(2) over MT(1) (MT(1)/MT(2) = 19) and compound 13 have good affinities for both MT(1) (Ki :28 nM) and MT(2) (Ki : 8 nM).
authors.affiliation: Institut de Chimie Organique et Analytique, Université d'Orléans, Rue de Chartres, UMR CNRS 6005, BP 6759, 45067 Orléans Cedex 2, France.
authors.forename: Saïd
authors.initials: S
authors.lastname: El Kazzouli
authors.forename: Amaury
authors.initials: A
authors.lastname: Griffon du Bellay
authors.forename: Sabine
authors.initials: S
authors.lastname: Berteina-Raboin
authors.forename: Philippe
authors.initials: P
authors.lastname: Delagrange
authors.forename: Daniel-Henry
authors.initials: DH
authors.lastname: Caignard
authors.forename: Gérald
authors.initials: G
authors.lastname: Guillaumet
mesh_terms: D000818:Animals; D016466:CHO Cells; D002460:Cell Line; D006224:Cricetinae; D003412:Cricetulus; D015195:Drug Design; D004353:Drug Evaluation, Preclinical; D006801:Humans; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D044094:Receptors, Melatonin / Q000187:drug effects* / Q000378:metabolism; D013055:Spectrophotometry, Infrared
chemical_list: D008024:Ligands; D011725:Pyridines; D044094:Receptors, Melatonin