2(3H)-benzoxazolone and bioisosters as "privileged scaffold" in the design of pharmacological probes.
(2005) Current Medicinal Chemistry — Vol. 12, n° 7, p. 877-885 (2005)
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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.
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Poupaert, J., Carato, P., & Colacino, E. (2005). 2(3H)-benzoxazolone and bioisosters as “privileged scaffold” in the design of pharmacological probes. Current Medicinal Chemistry, 12(7), 877-885. https://doi.org/10.2174/0929867053507388 (Original work published 2005)