title: Design and synthesis of 3-phenyl tetrahydronaphthalenic derivatives as new selective MT2 melatoninergic ligands.
abstract: Tetrahydronaphthalenic analogues of melatonin have been synthesized and evaluated as melatonin receptor ligands. Introduction of a phenyl substituent in the 3-position of the tetraline ring allows to obtain MT(2) selective ligands. Activity and MT(2) selectivity can be modulated with suitable modifications of the N-acyl substituent. The (+)-(RR)-cis enantiomer of the N-[2-(7-methoxy-3-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)ethyl]cyclobutyl carboxamide (14) is one of the most MT(2) selective ligands described until now and behaves as an antagonist.
authors.affiliation: Laboratoire de Chimie Thérapeutique, Faculté des Sciences Pharmaceutiques et Biologiques, Université de Lille 2, BP 83, 59006 Lille Cedex, France. syous@phare.univ-lille2.fr
authors.forename: Saíd
authors.initials: S
authors.lastname: Yous
authors.forename: Sophie
authors.initials: S
authors.lastname: Durieux-Poissonnier
authors.forename: Emmanuelle
authors.initials: E
authors.lastname: Lipka-Belloli
authors.forename: Halim
authors.initials: H
authors.lastname: Guelzim
authors.forename: Christophe
authors.initials: C
authors.lastname: Bochu
authors.forename: Valérie
authors.initials: V
authors.lastname: Audinot
authors.forename: Jean A
authors.initials: JA
authors.lastname: Boutin
authors.forename: Philippe
authors.initials: P
authors.lastname: Delagrange
authors.forename: Caroline
authors.initials: C
authors.lastname: Bennejean
authors.forename: Pierre
authors.initials: P
authors.lastname: Renard
authors.forename: Daniel
authors.initials: D
authors.lastname: Lesieur
mesh_terms: D000818:Animals; D001667:Binding, Competitive / Q000187:drug effects; D016466:CHO Cells; D006224:Cricetinae; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D016244:Guanosine 5'-O-(3-Thiotriphosphate) / Q000378:metabolism; D006168:Guinea Pigs; D006801:Humans; D007202:Indicators and Reagents; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008550:Melatonin / Q000031:analogs & derivatives* / Q000378:metabolism; D011956:Receptors, Cell Surface / Q000187:drug effects*; D018160:Receptors, Cytoplasmic and Nuclear / Q000187:drug effects*; D044094:Receptors, Melatonin; D013329:Structure-Activity Relationship; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D007202:Indicators and Reagents; D008024:Ligands; D011956:Receptors, Cell Surface; D018160:Receptors, Cytoplasmic and Nuclear; D044094:Receptors, Melatonin; D013764:Tetrahydronaphthalenes; D016244:Guanosine 5'-O-(3-Thiotriphosphate); C044556:2-iodomelatonin; D008550:Melatonin