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

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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.

Keywords: 2(3h)-benzothiazolinone; 2(3h)-benzoxazolone; bioisosterism; mixed affinity ligands; privileged scaffolds

Document Type: Review Article


Affiliations: 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.

Publication date: April 1, 2005

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  • Current Medicinal Chemistry covers all the latest and outstanding developments in medicinal chemistry and rational drug design. Each issue contains a series of timely in-depth reviews written by leaders in the field covering a range of the current topics in medicinal chemistry. Current Medicinal Chemistry is an essential journal for every medicinal chemist who wishes to be kept informed and up-to-date with the latest and most important developments.

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