6-Hydroxy-1,2,4-triazine-3,5(2H,4H)-dione Derivatives as Novel d -Amino Acid Oxidase Inhibitors

Journal of Medicinal Chemistry

Volumn 58, Issue 18, 2015, Pages 7258-7272

  Hin, Niyada ^a   Duvall, Bridget ^a   Ferraris, Dana ^a   Alt, Jesse ^a   Thomas, Ajit G ^a   Rais, Rana ^a,b   Rojas, Camilo ^a   Wu, Ying ^a   Wozniak, Krystyna M ^a   Slusher, Barbara S ^a,b   Tsukamoto, Takashi ^a,b  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 HYDROXY 1,2,4 TRIAZINE 3,5 (2H,4H) DIONE DERIVATIVE; 6 HYDROXY 2 (NAPHTHALEN 1 YLMETHYL) 1,2,4 TRIAZINE 3,5 (2H,4H) DIONE; DEXTRO SERINE; OXIDOREDUCTASE INHIBITOR; UNCLASSIFIED DRUG; 6-HYDROXY-2-(NAPHTHALEN-1-YLMETHYL)-1,2,4-TRIAZINE-3,5(2H,4H)-DIONE; DEXTRO AMINO ACID OXIDASE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; PROTEIN BINDING; SERINE; TRIAZINE DERIVATIVE;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG GLUCURONIDATION; DRUG METABOLISM; DRUG PENETRATION; DRUG STRUCTURE; DRUG SYNTHESIS; IC50; MAXIMUM PLASMA CONCENTRATION; MOUSE; NONHUMAN; PHARMACOPHORE; TIME TO MAXIMUM PLASMA CONCENTRATION; AGONISTS; ANIMAL; ANTAGONISTS AND INHIBITORS; BIOAVAILABILITY; BLOOD; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG INTERACTION; HUMAN; MALE; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

ANIMALS; BIOLOGICAL AVAILABILITY; CELL LINE; D-AMINO-ACID OXIDASE; DRUG INTERACTIONS; HUMANS; MALE; MICE; MODELS, MOLECULAR; PROTEIN BINDING; RECEPTORS, N-METHYL-D-ASPARTATE; SERINE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZINES;

EID: 84942362195     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b00482     Document Type: Article

References (33)

1. Nunes, E. A.; MacKenzie, E. M.; Rossolatos, D.; Perez-Parada, J.; Baker, G. B.; Dursun, S. M. D-serine and schizophrenia: an update Expert Rev. Neurother. 2012, 12, 801-812 10.1586/ern.12.65
2. Kantrowitz, J. T.; Malhotra, A. K.; Cornblatt, B.; Silipo, G.; Balla, A.; Suckow, R. F.; D'Souza, C.; Saksa, J.; Woods, S. W.; Javitt, D. C. High dose D-serine in the treatment of schizophrenia Schizophrenia Res. 2010, 121, 125-130 10.1016/j.schres.2010.05.012
3. Ganote, C. E.; Peterson, D. R.; Carone, F. A. The nature of D-serine - induced nephrotoxicity Am. J. Pathol. 1974, 77, 269-282
4. Curti, B.; Ronchi, S.; Simonetta, P. M., D- and L-Amino Acid Oxidases. In Chemistry and Biochemistry of Flavoenzyme; Muller, F., Ed. CRC Press: Boca Raton, FL, 1992; Vol. 3, pp 69-94.
5. Rais, R.; Thomas, A. G.; Wozniak, K.; Wu, Y.; Jaaro-Peled, H.; Sawa, A.; Strick, C. A.; Engle, S. J.; Brandon, N. J.; Rojas, C.; Slusher, B. S.; Tsukamoto, T. Pharmacokinetics of oral D-serine in D-amino acid oxidase knockout mice Drug Metab. Dispos. 2012, 40, 2067-2073 10.1124/dmd.112.046482
6. Maekawa, M.; Okamura, T.; Kasai, N.; Hori, Y.; Summer, K. H.; Konno, R. D-amino-acid oxidase is involved in D-serine-induced nephrotoxicity Chem. Res. Toxicol. 2005, 18, 1678-1682 10.1021/tx0500326
7. Sacchi, S.; Caldinelli, L.; Cappelletti, P.; Pollegioni, L.; Molla, G. Structure-function relationships in human D-amino acid oxidase Amino Acids 2012, 43, 1833-1850 10.1007/s00726-012-1345-4
8. Ferraris, D. V.; Tsukamoto, T. Recent advances in the discovery of D-amino acid oxidase inhibitors and their therapeutic utility in schizophrenia Curr. Pharm. Des. 2011, 17, 103-111 10.2174/138161211795049633
9. Sacchi, S.; Rosini, E.; Pollegioni, L.; Molla, G. D-amino acid oxidase inhibitors as a novel class of drugs for schizophrenia therapy Curr. Pharm. Des. 2013, 19, 2499-2511 10.2174/1381612811319140002
10. Adage, T.; Trillat, A. C.; Quattropani, A.; Perrin, D.; Cavarec, L.; Shaw, J.; Guerassimenko, O.; Giachetti, C.; Greco, B.; Chumakov, I.; Halazy, S.; Roach, A.; Zaratin, P. In vitro and in vivo pharmacological profile of AS057278, a selective D-amino acid oxidase inhibitor with potential anti-psychotic properties Eur. Neuropsychopharmacol. 2008, 18, 200-214 10.1016/j.euroneuro.2007.06.006
11. Sparey, T.; Abeywickrema, P.; Almond, S.; Brandon, N.; Byrne, N.; Campbell, A.; Hutson, P. H.; Jacobson, M.; Jones, B.; Munshi, S.; Pascarella, D.; Pike, A.; Prasad, G. S.; Sachs, N.; Sakatis, M.; Sardana, V.; Venkatraman, S.; Young, M. B. The discovery of fused pyrrole carboxylic acids as novel, potent D-amino acid oxidase (DAO) inhibitors Bioorg. Med. Chem. Lett. 2008, 18, 3386-3391 10.1016/j.bmcl.2008.04.020
12. Ferraris, D.; Duvall, B.; Ko, Y. S.; Thomas, A. G.; Rojas, C.; Majer, P.; Hashimoto, K.; Tsukamoto, T. Synthesis and biological evaluation of D-amino acid oxidase inhibitors J. Med. Chem. 2008, 51, 3357-3359 10.1021/jm800200u
13. Duplantier, A. J.; Becker, S. L.; Bohanon, M. J.; Borzilleri, K. A.; Chrunyk, B. A.; Downs, J. T.; Hu, L. Y.; El-Kattan, A.; James, L. C.; Liu, S.; Lu, J.; Maklad, N.; Mansour, M. N.; Mente, S.; Piotrowski, M. A.; Sakya, S. M.; Sheehan, S.; Steyn, S. J.; Strick, C. A.; Williams, V. A.; Zhang, L. Discovery, SAR, and pharmacokinetics of a novel 3-hydroxyquinolin-2(1H)-one series of potent D-amino acid oxidase (DAAO) inhibitors J. Med. Chem. 2009, 52, 3576-3585 10.1021/jm900128w
14. 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. 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, 839-843 10.1021/ml300212a
15. Katane, M.; Osaka, N.; Matsuda, S.; Maeda, K.; Kawata, T.; Saitoh, Y.; Sekine, M.; Furuchi, T.; Doi, I.; Hirono, S.; Homma, H. Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro J. Med. Chem. 2013, 56, 1894-1190 10.1021/jm3017865
16. Kawazoe, T.; Tsuge, H.; Imagawa, T.; Aki, K.; Kuramitsu, S.; Fukui, K. Structural basis of D-DOPA oxidation by D-amino acid oxidase: alternative pathway for dopamine biosynthesis Biochem. Biophys. Res. Commun. 2007, 355, 385-391 10.1016/j.bbrc.2007.01.181
17. Raje, M.; Hin, N.; Duvall, B.; Ferraris, D. V.; Berry, J. F.; Thomas, A. G.; Alt, J.; Rojas, C.; Slusher, B. S.; Tsukamoto, T. Synthesis of kojic acid derivatives as secondary binding site probes of d-amino acid oxidase Bioorg. Med. Chem. Lett. 2013, 23, 3910-3913 10.1016/j.bmcl.2013.04.062
18. Hondo, T.; Warizaya, M.; Niimi, T.; Namatame, I.; Yamaguchi, T.; Nakanishi, K.; Hamajima, T.; Harada, K.; Sakashita, H.; Matsumoto, Y.; Orita, M.; Takeuchi, M. 4-Hydroxypyridazin-3(2H)-one derivatives as novel D-amino acid oxidase inhibitors J. Med. Chem. 2013, 56, 3582-3592 10.1021/jm400095b
19. Hopkins, S. C.; Heffernan, M. L.; Saraswat, L. D.; Bowen, C. A.; Melnick, L.; Hardy, L. W.; Orsini, M. A.; Allen, M. S.; Koch, P.; Spear, K. L.; Foglesong, R. J.; Soukri, M.; Chytil, M.; Fang, Q. K.; Jones, S. W.; Varney, M. A.; Panatier, A.; Oliet, S. H.; Pollegioni, L.; Piubelli, L.; Molla, G.; Nardini, M.; Large, T. H. Structural, kinetic, and pharmacodynamic mechanisms of D-amino acid oxidase inhibition by small molecules J. Med. Chem. 2013, 56, 3710-3724 10.1021/jm4002583
20. Terry-Lorenzo, R. T.; Chun, L. E.; Brown, S. P.; Heffernan, M. L.; Fang, Q. K.; Orsini, M. A.; Pollegioni, L.; Hardy, L. W.; Spear, K. L.; Large, T. H. Novel human D-amino acid oxidase inhibitors stabilize an active site lid open conformation Biosci. Rep. 2014, 34, 487-499 10.1042/BSR20140071
21. Lange, J. H.; Venhorst, J.; van Dongen, M. J.; Frankena, J.; Bassissi, F.; de Bruin, N. M.; Besten, C.; de Beer, S. B.; Oostenbrink, C.; Markova, N.; Kruse, C. G. Biophysical and physicochemical methods differentiate highly ligand-efficient human D-amino acid oxidase inhibitors Eur. J. Med. Chem. 2011, 46, 4808-4819 10.1016/j.ejmech.2011.04.023
22. Zimmermann, S. C.; Rais, R.; Alt, J.; Burzynski, C.; Slusher, B. S.; Tsukamoto, T. Structure-metabolism relationships in the glucuronidation of D-amino acid oxidase inhibitors ACS Med. Chem. Lett. 2014, 5, 1251-1253 10.1021/ml500335z
23. Zajac, M.; Muszalska, I. Mechanism of ceftriaxone degradation in aqueous solution Acta Polym. Pharm. 1998, 55, 35-39
24. Dudfield, P. J.; Le, V.-D.; Lindell, S. D.; Rees, C. W. Synthesis of C-ribosyl imidazo[2,1-f ][1,2,4]triazines as inhibitors of adenosine and AMP deaminases J. Chem. Soc., Perkin Trans. 1 1999, 2929-2936 10.1039/a904065j
25. Pontillo, J.; Guo, Z.; Wu, D.; Struthers, R. S.; Chen, C. Synthesis of aryl-1,2,4-triazine-3,5-diones as antagonists of the gonadotropin-releasing hormone receptor Bioorg. Med. Chem. Lett. 2005, 15, 4363-4366 10.1016/j.bmcl.2005.06.057
26. Leroy, I.; Dupont-Passelaigue, E.; Valeille, K.; Rival, Y.; Junquero, D. Derivatives of triazines and uracils, their preparation and their application in human therapeutics. U.S. Patent 8,618,287, Dec 31, 2013.
27. Jensen, K. A.; Anthoni, U.; Kägi, B.; Larsen, C.; Pedersen, C. T.; Rosen, U. Studies of thioacids and their derivatives. IX. Thiosemicarbazides Acta Chem. Scand. 1968, 22, 1-50 10.3891/acta.chem.scand.22-0001
28. Branch, C. L.; Eggleston, D. S.; Haltiwanger, R. C.; Kaura, A. C.; Tyler, J. W. Synthesis of 6-Hydroxy-2-methyl-3-thioxo-2H-1,2,4-triazin-5-one Synth. Commun. 1996, 26, 2075-2084
29. Nagata, Y.; Shimojo, T.; Akino, T. D-amino acid oxidase in mouse liver-II Comp. Biochem. Physiol. B 1988, 91, 503-504 10.1016/0305-0491(88)90012-0
30. Trott, O.; Olson, A. J. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading J. Comput. Chem. 2010, 31, 455-461 10.1002/jcc.21334
31. Kawazoe, T.; Tsuge, H.; Pilone, M. S.; Fukui, K. Crystal structure of human D-amino acid oxidase: context-dependent variability of the backbone conformation of the VAAGL hydrophobic stretch located at the si-face of the flavin ring Protein Sci. 2006, 15, 2708-2717 10.1110/ps.062421606
32. Cook, S. P.; Galve-Roperh, I.; Martinez del Pozo, A.; Rodriguez-Crespo, I. Direct calcium binding results in activation of brain serine racemase J. Biol. Chem. 2002, 277, 27782-27792 10.1074/jbc.M111814200
33. Berna, M. J.; Ackermann, B. L. Quantification of serine enantiomers in rat brain microdialysate using Marfeys reagent and LC/MS/MS J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2007, 846, 359-363 10.1016/j.jchromb.2006.08.029