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2(3H)-Benzoxazolone and Bioisosters as “Privileged Scaffold” in the Design of Pharmacological Probes

[ Vol. 12 , Issue. 7 ]


Jacques Poupaert, Pascal Carato and Evelina Colacino   Pages 877 - 885 ( 9 )


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 pKas, 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.


bioisosterism,privileged scaffolds,2(3h)-benzoxazolone,2(3h)-benzothiazolinone,mixed affinity ligands


, , Unite de Chimie Pharmaceutique et Radiopharmacie, Ecole de Pharmacie, Faculte de Medecine, Universite Catholique de Louvain, (UCL-CMFA 7340), 73 Avenue Emmanuel Mounier, Brussels, B-1200 Belgium.

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