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Synthesis and Biological Evaluation of d-Amino Acid Oxidase Inhibitors

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MGI Pharma, Inc., 6611 Tributary Street, Baltimore, Maryland 21224, and Division of Clinical Neuroscience, Chiba University Center for Forensic Mental Health, 1-8-1 Inohana, Chiba 260-8670, Japan
* To whom correspondence should be addressed. Phone: 410-631-6762 . Fax: 410-631-6804 . E-mail: [email protected]
†MGI Pharma, Inc.
‡Chiba University Center for Forensic Mental Health.
Cite this: J. Med. Chem. 2008, 51, 12, 3357–3359
Publication Date (Web):May 29, 2008
Copyright © 2008 American Chemical Society

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    Abstract Image

    d-Amino acid oxidase (DAAO) catalyzes the oxidation of d-amino acids including d-serine, a full agonist at the glycine site of the NMDA receptor. A series of benzo[d]isoxazol-3-ol derivatives were synthesized and evaluated as DAAO inhibitors. Among them, 5-chloro-benzo[d]isoxazol-3-ol (CBIO) potently inhibited DAAO with an IC50 in the submicromolar range. Oral administration of CBIO in conjunction with d-serine enhanced the plasma and brain levels of d-serine in rats compared to the oral administration of d-serine alone.

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    Synthetic procedures for CMBI and 3an, elemental analysis data, in vitro d-amino acid oxidase assay method, and in vivo experimental procedures. This material is available free of charge via the Internet at

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