Synthesis and biological evaluation of D-amino acid oxidase inhibitors

Dana Ferraris; Bridget Duvall; Yao Sen Ko; Ajit G. Thomas; Camilo Rojas; Pavel Majer; Kenji Hashimoto; Takashi Tsukamoto

doi:10.1021/jm800200u

Synthesis and biological evaluation of D-amino acid oxidase inhibitors

Dana Ferraris, Bridget Duvall, Yao Sen Ko, Ajit G. Thomas, Camilo Rojas, Pavel Majer, Kenji Hashimoto, Takashi Tsukamoto

Research output: Contribution to journal › Article › peer-review

110 Scopus citations

Abstract

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-chlorobenzo[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.

Original language	English (US)
Pages (from-to)	3357-3359
Number of pages	3
Journal	Journal of medicinal chemistry
Volume	51
Issue number	12
DOIs	https://doi.org/10.1021/jm800200u
State	Published - Jun 26 2008
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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title = "Synthesis and biological evaluation of D-amino acid oxidase inhibitors",

abstract = "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-chlorobenzo[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.",

author = "Dana Ferraris and Bridget Duvall and Ko, {Yao Sen} and Thomas, {Ajit G.} and Camilo Rojas and Pavel Majer and Kenji Hashimoto and Takashi Tsukamoto",

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doi = "10.1021/jm800200u",

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T1 - Synthesis and biological evaluation of D-amino acid oxidase inhibitors

AU - Ferraris, Dana

AU - Duvall, Bridget

AU - Ko, Yao Sen

AU - Thomas, Ajit G.

AU - Rojas, Camilo

AU - Majer, Pavel

AU - Hashimoto, Kenji

AU - Tsukamoto, Takashi

PY - 2008/6/26

Y1 - 2008/6/26

N2 - 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-chlorobenzo[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.

AB - 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-chlorobenzo[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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Synthesis and biological evaluation of D-amino acid oxidase inhibitors

Abstract

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