title: Design and synthesis of 1-(2-alkanamidoethyl)-6-methoxy-7-azaindole derivatives as potent melatonin agonists.
abstract: A series of 7-azaindolic ligands bearing a methoxy group and a N-acetyl chain as melatoninergic pharmacophores were synthesized and their binding affinities towards MT(1) and MT(2) receptors were evaluated. Compounds 7a-c and 12 (cyclohexyl ring connected at C-2 and C-3 position) appears as important melatonin MT(2) and MT(1) receptors agonists. On the other hand, the presence of basic groups (amines) at position C-3 was detrimental to the melatoninergic affinities.
authors.affiliation: Institut de Chimie Organique et Analytique, Université d'Orléans, UMR-CNRS 6005, BP 6759, rue de Chartres, 45067 Orléans Cedex 2, France.
authors.forename: Matthieu
authors.initials: M
authors.lastname: Jeanty
authors.forename: Franck
authors.initials: F
authors.lastname: Suzenet
authors.forename: Philippe
authors.initials: P
authors.lastname: Delagrange
authors.forename: Olivier
authors.initials: O
authors.lastname: Nosjean
authors.forename: Jean A
authors.initials: JA
authors.lastname: Boutin
authors.forename: Daniel H
authors.initials: DH
authors.lastname: Caignard
authors.forename: Gérald
authors.initials: G
authors.lastname: Guillaumet
mesh_terms: D015195:Drug Design; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D011485:Protein Binding; D044122:Receptor, Melatonin, MT1 / Q000819:agonists* / Q000378:metabolism; D044123:Receptor, Melatonin, MT2 / Q000819:agonists* / Q000378:metabolism
chemical_list: C023422:7-azaindole dimer; D007211:Indoles; D044122:Receptor, Melatonin, MT1; D044123:Receptor, Melatonin, MT2