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Berry JF, Ferraris DV, Duvall B, et al. Synthesis and SAR of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones as Inhibitors of D-Amino Acid Oxidase. ACS Med Chem Lett. 2012;3(10):839-843doi: 10.1021/ml300212a.
Berry, J. F., Ferraris, D. V., Duvall, B., Hin, N., Rais, R., Alt, J., Thomas, A. G., Rojas, C., Hashimoto, K., Slusher, B. S., & Tsukamoto, T. (2012). Synthesis and SAR of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones as Inhibitors of D-Amino Acid Oxidase. ACS medicinal chemistry letters, 3(10), 839-843. https://doi.org/10.1021/ml300212a
Berry, James F, et al. "Synthesis and SAR of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones as Inhibitors of D-Amino Acid Oxidase." ACS medicinal chemistry letters vol. 3,10 (2012): 839-843. doi: https://doi.org/10.1021/ml300212a
Berry JF, Ferraris DV, Duvall B, Hin N, Rais R, Alt J, Thomas AG, Rojas C, Hashimoto K, Slusher BS, Tsukamoto T. Synthesis and SAR of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones as Inhibitors of D-Amino Acid Oxidase. ACS Med Chem Lett. 2012 Oct 11;3(10):839-843. doi: 10.1021/ml300212a. Epub 2012 Sep 16. PMID: 23243487; PMCID: PMC3519437.
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ACS Med Chem Lett. 2012 Oct 11;3(10):839-843. doi: 10.1021/ml300212a. Epub 2012 Sep 16.

Synthesis and SAR of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones as Inhibitors of D-Amino Acid Oxidase.

ACS medicinal chemistry letters

James F Berry, Dana V Ferraris, Bridget Duvall, Niyada Hin, Rana Rais, Jesse Alt, Ajit G Thomas, Camilo Rojas, Kenji Hashimoto, Barbara S Slusher, Takashi Tsukamoto

Affiliations

  1. Department of Neurology, Johns Hopkins University, Baltimore, MD 21205, United States.

PMID: 23243487 PMCID: PMC3519437 DOI: 10.1021/ml300212a

Abstract

A series of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones were synthesized and evaluated for their ability to inhibit human and porcine forms of D-amino acid oxidase (DAAO). Inhibitory potency is largely dependent on the size and position of substituents on the benzene ring with IC(50) values of the compounds ranging from 70 nM to greater than 100 µM. Structure-activity relationships of this new class of DAAO inhibitors will be presented in detail along with comparisons to previously published SAR data from other classes of DAAO inhibitors. Some of these compounds were given to mice orally together with D-serine to assess their effects on plasma D-serine pharmacokinetics.

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