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Synthesis and Biochemical Evaluation of N-(4-Phenylthiazol-2-yl)benzenesulfonamides as High-Affinity Inhibitors of Kynurenine 3-Hydroxylase
Open accessAbstract
In this paper we describe the synthesis, structure-activity relationship (SAR), and biochemical characterization of N-(4-phenylthiazol-2-yl)benzenesulfonamides as inhibitors of kynurenine 3-hydroxylase. The compounds 3,4-dimethoxy-N-[4-(3-nitrophenyl)thiazol-2-yl]benzenesulfonamide 16 (IC50 = 37 nM, Ro-61-8048) and 4-amino-N-[4-[2-fluoro-5-(trifluoromethyl)phenyl]-thiazol-2-yl] benzenesulfonamide 20 (IC50 = 19 nM) were found to be high-affinity inhibitors of this enzyme in vitro. In addition, both compounds blocked rat and gerbil kynurenine 3-hydroxylase after oral administration, with ED50's in the 3-5 mumol/kg range in gerbil brain. In a microdialysis experiment in rats, 16 dose dependently increased kynurenic acid concentration in the extracellular hippocampal fluid. A dose of 100 mumol/kg po led to a 7.5-fold increase in kynurenic acid outflow. These new compounds should allow detailed investigation of the pathophysiological role of the kynurenine pathway after neuronal injury.
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Cited by
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Platten, M., Nollen, E. A. A., Röhrig, U. F., Fallarino, F., & Opitz, C. A. (2019) · Nature Reviews Drug Discovery · doi:10.1038/s41573-019-0016-5 · Cited by 1,586
Kynurenines in the mammalian brain: when physiology meets pathology
Schwarcz, R., Bruno, J. P., Muchowski, P. J., & Wu, H.-Q. (2012) · Nature Reviews Neuroscience · doi:10.1038/nrn3257 · Cited by 1,530
Endogenous kynurenines as targets for drug discovery and development
Stone, T. W., & Darlington, L. G. (2002) · Nature Reviews Drug Discovery · doi:10.1038/nrd870 · Cited by 768
Kynurenines in the CNS: recent advances and new questions
Vécsei, L., Szalárdy, L., Fülöp, F., & Toldi, J. (2013) · Nature Reviews Drug Discovery · doi:10.1038/nrd3793 · Cited by 641
Interleukin-1β: A New Regulator of the Kynurenine Pathway Affecting Human Hippocampal Neurogenesis
Zunszain, P. A., Anacker, C., Cattaneo, A., Choudhury, S., Musaelyan, K., Myint, A. M., Thuret, S., Price, J., & Pariante, C. M. (2012) · Neuropsychopharmacology · doi:10.1038/npp.2011.277 · Cited by 388
Metadata
- Authors
- Röver, S., Cesura, A. M., Huguenin, P., Kettler, R., & Szente, A.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1997-12-01
- Volume
- 40
- Issue
- 26
- Pages
- 4378-4385
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W1983052331
- Cited by
- 211
- References
- 0
- FWCI
- 3.33
- Type
- journal article
- Language
- en
- Open access
- green
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- Röver, S., Cesura, A. M., Huguenin, P., Kettler, R., & Szente, A. (1997). Synthesis and Biochemical Evaluation of N-(4-Phenylthiazol-2-yl)benzenesulfonamides as High-Affinity Inhibitors of Kynurenine 3-Hydroxylase. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm970467t
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