title: 2(3H)-benzoxazolone and bioisosters as "privileged scaffold" in the design of pharmacological probes.
abstract: The 2(3H)-benzoxazolone heterocycle and its bioisosteric surrogates (such as 2(3H)-benzothiazolinone, benzoxazinone, etc.) have received considerable attention from the medicinal chemists owing to their capacity to mimic a phenol or a catechol moiety in a metabolically stable template. These heterocycles and pyrocatechol have indeed similar pKa's, electronic charge distribution, and chemical reactivity. Therapeutic applications of this template are very broad, and range from analgesic anti-inflammatory compounds (including PPAR-gamma antagonists) to antipsychotic and neuroprotective anticonvulsant compounds. High affinity ligands have been obtained also for dopaminergic (D2 and D4), serotoninergic (5-HT1A and 5-HT-2A), sigma-1 and sigma-2 receptors. Owing to the high number of positive hits encountered with this heterocycle and its congeners, 2(3H)-benzoxazolone template certainly deserves the title of "privileged scaffold" in medicinal chemistry.
authors.affiliation: Unité de Chimie Pharmaceutique et Radiopharmacie, Ecole de Pharmacie, Université Catholique de Louvain, (UCL-CMFA 7340), Brussels B-1200, Belgium. poupaert@cmfa.ucl.ac.be
authors.forename: Jacques
authors.initials: J
authors.lastname: Poupaert
authors.forename: Pascal
authors.initials: P
authors.lastname: Carato
authors.forename: Evelina
authors.initials: E
authors.lastname: Colacino
authors.forename: Saïd
authors.initials: S
authors.lastname: Yous
mesh_terms: D001583:Benzoxazoles / Q000737:chemistry* / Q000494:pharmacology* / Q000627:therapeutic use; D006801:Humans; D008024:Ligands; D008958:Models, Molecular; D015335:Molecular Probes / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D015394:Molecular Structure
chemical_list: D001583:Benzoxazoles; D008024:Ligands; D015335:Molecular Probes; C017057:benzoxazolone