1: Curr Med Chem. 2005;12(7):877-85. Erratum in: Curr Med Chem. 2005;12(26):3163. Yous, Said [added]. 2(3H)-benzoxazolone and bioisosters as "privileged scaffold" in the design of pharmacological probes. Poupaert J, Carato P, Colacino E, Yous S. Unite de Chimie Pharmaceutique et Radiopharmacie, Ecole de Pharmacie, Universite Catholique de Louvain, (UCL-CMFA 7340), Brussels B-1200, Belgium. poupaert@cmfa.ucl.ac.be 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. Publication Types: Review PMID: 15853716 [PubMed - indexed for MEDLINE]