title: Synthesis and biological activity of a novel class nicotinic acetylcholine receptors (nAChRs) ligands structurally related to anatoxin-a.
abstract: The introduction of the isoxazole ring as bioisosteric replacement of the acetyl group of anatoxin-a led to a new series of derivatives binding to nicotinic acetylcholine receptors. Bulkier substitutions than methyl at the 3 position of isoxazole were shown to be detrimental for the activity. The binding potency of the most interesting compounds with α1, α7 and α3β4 receptor subtypes, was, anyway, only at micromolar level. Moreover, differently from known derivatives with pyridine, isoxazole condensed to azabicyclo ring led to no activity.
authors.affiliation: Department of Pharmaceutical Sciences, University of Ferrara, Via Fossato di Mortara 17/19, 44121 Ferrara, Italy. smd@unife.it
authors.forename: Daniele
authors.initials: D
authors.lastname: Simoni
authors.forename: Riccardo
authors.initials: R
authors.lastname: Rondanin
authors.forename: Paolo
authors.initials: P
authors.lastname: Marchetti
authors.forename: Cinzia
authors.initials: C
authors.lastname: Rullo
authors.forename: Riccardo
authors.initials: R
authors.lastname: Baruchello
authors.forename: Giuseppina
authors.initials: G
authors.lastname: Grisolia
authors.forename: Giuseppina
authors.initials: G
authors.lastname: Barbato
authors.forename: Riccardo
authors.initials: R
authors.lastname: Giovannini
authors.forename: Carla
authors.initials: C
authors.lastname: Marchioro
authors.forename: Anna Maria
authors.initials: AM
authors.lastname: Capelli
authors.forename: Caterina
authors.initials: C
authors.lastname: Virginio
authors.forename: Andrea
authors.initials: A
authors.lastname: Bozzoli
authors.forename: Pier Andrea
authors.initials: PA
authors.lastname: Borea
authors.forename: Stefania
authors.initials: S
authors.lastname: Merighi
authors.forename: Daniele
authors.initials: D
authors.lastname: Donati
mesh_terms: D060326:Chemistry Techniques, Synthetic; D000087522:Cyanobacteria Toxins; D004305:Dose-Response Relationship, Drug; D008024:Ligands; D008968:Molecular Conformation; D011978:Receptors, Nicotinic / Q000378:metabolism*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014326:Tropanes / Q000737:chemistry*
chemical_list: D000087522:Cyanobacteria Toxins; D008024:Ligands; D011978:Receptors, Nicotinic; D014326:Tropanes; C509783:anatoxin a