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]