메뉴 건너뛰기




Volumn 56, Issue 9, 2013, Pages 3582-3592

4-Hydroxypyridazin-3(2 H)-one derivatives as novel d-amino acid oxidase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 5(2 PHENYLETHYLPYRIDIN) 2(1H) ONE; 3 HYDROXY 5(2 PHENYLETHYLPYRIDINE) 2(1H) ONE DERIVATIVE; 3 HYDROXY PYRIDINE 2(1H) ONE DERIVATIVE; 4 HYDROXY 6 (PHENOXYMETHYLPYRIDAZIN) 3(2H) ONE; 4 HYDROXY 6(1 PHENYLETHYLPYRIDAZIN) 3(2H) ONE; 4 HYDROXY 6(2 PHENYLETHYLPYRIDAZIN) 3(2H) ONE; 4 HYDROXY 6(3 PHENYLPROPYLPYRIDAZIN) 3(2H) ONE; 4 HYDROXY 6[2(2 (TRIFLUOROMETHYLPHENYLETHYLPYRIDAZIN))] 3(2H) ONE; 4 HYDROXY 6[2(3 (TRIFLUOROMETHYLPHENYLETHYLPYRIDAZIN))] 3(2H) ONE; 4 HYDROXY 6[2(3 METHOXYPHENYLETHYLPYRIDAZIN)] 3(2H) ONE; 4 HYDROXY 6[2(4 (TRIFLUOROMETHYLPHENYLETHYLPYRIDAZIN))] 3(2H) ONE; 4 HYDROXY 6[2(4 METHOXYPHENYLETHYLPYRIDAZIN)] 3(2H) ONE; 4 HYDROXYPYRIDAZIN 3(2H) ONE DERIVATIVE; 6 ((E) 2(4 CHLOROPHENYLVINYL)) 4 HYDROXYPYRIDAZIN 3(2H) ONE; 6 2(3,5 DIFLUOROPHENYLETHYL) 4 HYDROXYPYRIDAZIN 3(2H) ONE DERIVATIVE; 6 CYCLOHEXYL 4 HYDROXYPYRIDAZIN 3(2H) ONE; 6(2 CYCLOHEXYLETHYL) 4 HYDROXYPYRIDAZIN 3(2H) ONE; 6(3,3 DIMETHYLBUTYL) 4 HYDROXYPYRIDAZIN 3(2H) ONE; 6[2(2 FLUOROPHENYLETHYL)] 4 HYDROXYPYRIDAZIN 3(2H) ONE; 6[2(3 FLUOROPHENYLETHYL)] 4 HYDROXYPYRIDAZIN 3(2H) ONE; 6[2(3,5 DIFLUOROPHENYLETHYL)] 4 HYDROXYPYRIDAZIN 3(2H) ONE; 6[2(4 CHLOROPHENYLETHYL)] 4 HYDROXYPYRIDAZIN 3(2H) ONE; 6[2(4 FLUOROPHENYLETHYL)] 4 HYDROXYPYRIDAZIN 3(2H) ONE; DEXTRO AMINO ACID OXIDASE; DEXTRO AMINO ACID OXIDASE INHIBITOR; DIZOCILPINE; OXIDOREDUCTASE INHIBITOR; PYRIDAZINE DERIVATIVE; QUERCETIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 84877704487     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400095b     Document Type: Article
Times cited : (41)

References (44)
  • 1
    • 0025952455 scopus 로고
    • Recent advances in the phencyclidine model of schizophrenia
    • Javitt, D. C.; Zukin, S. R. Recent advances in the phencyclidine model of schizophrenia Am. J. Psychiatry 1991, 148, 1301-1308
    • (1991) Am. J. Psychiatry , vol.148 , pp. 1301-1308
    • Javitt, D.C.1    Zukin, S.R.2
  • 7
    • 0032403626 scopus 로고    scopus 로고
    • D-Serine added to antipsychotics for the treatment of schizophrenia
    • Tsai, G.; Yang, P.; Chung, L.-C.; Lange, N.; Coyle, J. T. d-Serine added to antipsychotics for the treatment of schizophrenia Biol. Psychiatry 1998, 44, 1081-1089
    • (1998) Biol. Psychiatry , vol.44 , pp. 1081-1089
    • Tsai, G.1    Yang, P.2    Chung, L.-C.3    Lange, N.4    Coyle, J.T.5
  • 11
    • 43549109188 scopus 로고    scopus 로고
    • Mice lacking d-amino acid oxidase activity exhibit marked reduction of methamphetamine-induced stereotypy
    • Hashimoto, A.; Konno, R.; Yano, H.; Yoshikawa, M.; Tamaki, R.; Matsumoto, H.; Kobayashi, H. Mice lacking d-amino acid oxidase activity exhibit marked reduction of methamphetamine-induced stereotypy Eur. J. Pharmacol. 2008, 586, 221-225
    • (2008) Eur. J. Pharmacol. , vol.586 , pp. 221-225
    • Hashimoto, A.1    Konno, R.2    Yano, H.3    Yoshikawa, M.4    Tamaki, R.5    Matsumoto, H.6    Kobayashi, H.7
  • 12
    • 13244260784 scopus 로고    scopus 로고
    • Mice lacking d-amino acid oxidase activity display marked attenuation of stereotypy and ataxia induced by MK-801
    • Hashimoto, A.; Yoshikawa, M.; Niwa, A.; Konno, R. Mice lacking d-amino acid oxidase activity display marked attenuation of stereotypy and ataxia induced by MK-801 Brain Res. 2005, 1033, 210-215
    • (2005) Brain Res. , vol.1033 , pp. 210-215
    • Hashimoto, A.1    Yoshikawa, M.2    Niwa, A.3    Konno, R.4
  • 13
    • 33745689721 scopus 로고    scopus 로고
    • G72/G30 in Schizophrenia and Bipolar Disorder: Review and Meta-analysis
    • Detera-Wadleigh, S. D.; McMahon, F. J. G72/G30 in Schizophrenia and Bipolar Disorder: Review and Meta-analysis Biol. Psychiatry 2006, 60, 106-114
    • (2006) Biol. Psychiatry , vol.60 , pp. 106-114
    • Detera-Wadleigh, S.D.1    McMahon, F.J.2
  • 14
    • 0343478442 scopus 로고
    • Flavoenzyme catalysis. Substrate-competitive inhibition of d-amino acid oxidase
    • Frisell, W. R.; Lowe, H. J.; Hellerman, L. Flavoenzyme catalysis. Substrate-competitive inhibition of d-amino acid oxidase J. Biol. Chem. 1956, 223, 75-83
    • (1956) J. Biol. Chem. , vol.223 , pp. 75-83
    • Frisell, W.R.1    Lowe, H.J.2    Hellerman, L.3
  • 21
    • 46849089254 scopus 로고    scopus 로고
    • Recent Developments in Fragment-Based Drug Discovery
    • Congreve, M.; Chessari, G.; Tisi, D.; Woodhead, A. J. Recent Developments in Fragment-Based Drug Discovery J. Med. Chem. 2008, 51, 3661-3680
    • (2008) J. Med. Chem. , vol.51 , pp. 3661-3680
    • Congreve, M.1    Chessari, G.2    Tisi, D.3    Woodhead, A.J.4
  • 23
    • 33847133461 scopus 로고    scopus 로고
    • Structural basis of d-DOPA oxidation by d-amino acid oxidase: Alternative pathway for dopamine biosynthesis
    • 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
    • (2007) Biochem. Biophys. Res. Commun. , vol.355 , pp. 385-391
    • Kawazoe, T.1    Tsuge, H.2    Imagawa, T.3    Aki, K.4    Kuramitsu, S.5    Fukui, K.6
  • 25
    • 79953315208 scopus 로고    scopus 로고
    • Recent Advances in the Discovery of d-Amino Acid Oxidase Inhibitors and Their Therapeutic Utility in Schizophrenia
    • 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
    • (2011) Curr. Pharm. Des. , vol.17 , pp. 103-111
    • Ferraris, D.V.1    Tsukamoto, T.2
  • 26
    • 84861339892 scopus 로고    scopus 로고
    • A novel glycine transporter-1 (GlyT1) inhibitor, ASP2535 (4-[3-isopropyl-5-(6-phenyl-3-pyridyl)-4 H-1,2,4-triazol-4-yl]-2,1,3- benzoxadiazole), improves cognition in animal models of cognitive impairment in schizophrenia and Alzheimer's disease
    • Harada, K.; Nakato, K.; Yarimizu, J.; Yamazaki, M.; Morita, M.; Takahashi, S.; Aota, M.; Saita, K.; Doihara, H.; Sato, Y.; Yamaji, T.; Ni, K.; Matsuoka, N. A novel glycine transporter-1 (GlyT1) inhibitor, ASP2535 (4-[3-isopropyl-5-(6-phenyl-3-pyridyl)-4 H-1,2,4-triazol-4-yl]-2,1,3- benzoxadiazole), improves cognition in animal models of cognitive impairment in schizophrenia and Alzheimer's disease Eur. J. Pharmacol. 2012, 685, 59-69
    • (2012) Eur. J. Pharmacol. , vol.685 , pp. 59-69
    • Harada, K.1    Nakato, K.2    Yarimizu, J.3    Yamazaki, M.4    Morita, M.5    Takahashi, S.6    Aota, M.7    Saita, K.8    Doihara, H.9    Sato, Y.10    Yamaji, T.11    Ni, K.12    Matsuoka, N.13
  • 27
    • 0030896029 scopus 로고    scopus 로고
    • Huperzine A, a novel promising acetylcholinesterase inhibitor
    • Cheng, D. H.; Ren, H.; Tang, X. C. Huperzine A, a novel promising acetylcholinesterase inhibitor Neuroreport 1996, 8, 97-101
    • (1996) Neuroreport , vol.8 , pp. 97-101
    • Cheng, D.H.1    Ren, H.2    Tang, X.C.3
  • 28
    • 0030845192 scopus 로고    scopus 로고
    • Dose-Dependent Effects of the Dopamine D1 Receptor Agonists A77636 or SKF81297 on Spatial Working Memory in Aged Monkeys
    • Cai, J. X.; Arnsten, A. F. T. Dose-Dependent Effects of the Dopamine D1 Receptor Agonists A77636 or SKF81297 on Spatial Working Memory in Aged Monkeys J. Pharmacol. Exp. Ther. 1997, 283, 183-189
    • (1997) J. Pharmacol. Exp. Ther. , vol.283 , pp. 183-189
    • Cai, J.X.1    Arnsten, A.F.T.2
  • 29
    • 24344434746 scopus 로고    scopus 로고
    • The selective PDE5 inhibitor, sildenafil, improves object memory in Swiss mice and increases cGMP Levels in hippocampal slices
    • Rutten, K.; Vente, J. D.; Şik, A.; Ittersum, M. M.-V.; Prickaerts, J.; Blokland, A. The selective PDE5 inhibitor, sildenafil, improves object memory in Swiss mice and increases cGMP Levels in hippocampal slices Behav. Brain Res. 2005, 164, 11-16
    • (2005) Behav. Brain Res. , vol.164 , pp. 11-16
    • Rutten, K.1    Vente, J.D.2    Şik, A.3    Ittersum, M.M.-V.4    Prickaerts, J.5    Blokland, A.6
  • 30
    • 79958138448 scopus 로고    scopus 로고
    • Inverted-U-Shaped Dopamine Actions on Human Working Memory and Cognitive Control
    • Cools, R.; D'Esposito, M. Inverted-U-Shaped Dopamine Actions on Human Working Memory and Cognitive Control Biol. Psychiatry 2011, 69, e113-e125
    • (2011) Biol. Psychiatry , vol.69
    • Cools, R.1    D'Esposito, M.2
  • 31
    • 0024432825 scopus 로고
    • Structural requirements for activation of the glycine coagonist site of N-methyl-d-aspartate receptors expressed in Xenopus oocytes
    • McBain, C. J.; Kleckner, N. W.; Wyrick, S.; Dingledine, R. Structural requirements for activation of the glycine coagonist site of N-methyl-d-aspartate receptors expressed in Xenopus oocytes Mol. Pharmacol. 1989, 36, 556-565
    • (1989) Mol. Pharmacol. , vol.36 , pp. 556-565
    • McBain, C.J.1    Kleckner, N.W.2    Wyrick, S.3    Dingledine, R.4
  • 32
    • 0035811252 scopus 로고    scopus 로고
    • Determination of free d-aspartic acid, d-serine and d-alanine in the brain of mutant mice lacking d-amino acid oxidase activity
    • Morikawa, A.; Hamase, K.; Inoue, T.; Konno, R.; Niwa, A.; Zaitsu, K. Determination of free d-aspartic acid, d-serine and d-alanine in the brain of mutant mice lacking d-amino acid oxidase activity J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2001, 757, 119-125
    • (2001) J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. , vol.757 , pp. 119-125
    • Morikawa, A.1    Hamase, K.2    Inoue, T.3    Konno, R.4    Niwa, A.5    Zaitsu, K.6
  • 33
    • 24944504370 scopus 로고    scopus 로고
    • Sensitive Determination of d-Amino Acids in Mammals and the Effect of d-Amino Acid Oxidase Activity on Their Amounts
    • Hamase, K.; Konno, R.; Morikawa, A.; Zaitsu, K. Sensitive Determination of d-Amino Acids in Mammals and the Effect of d-Amino Acid Oxidase Activity on Their Amounts Biol. Pharm. Bull. 2005, 28, 1578-1584
    • (2005) Biol. Pharm. Bull. , vol.28 , pp. 1578-1584
    • Hamase, K.1    Konno, R.2    Morikawa, A.3    Zaitsu, K.4
  • 35
    • 67349116852 scopus 로고    scopus 로고
    • Co-administration of a d-Amino Acid Oxidase Inhibitor Potentiates the Efficacy of d-Serine in Attenuating Prepulse Inhibition Deficits after Administration of Dizocilpine
    • Hashimoto, K.; Fujita, Y.; Horio, M.; Kunitachi, S.; Iyo, M.; Ferraris, D.; Tsukamoto, T. Co-administration of a d-Amino Acid Oxidase Inhibitor Potentiates the Efficacy of d-Serine in Attenuating Prepulse Inhibition Deficits After Administration of Dizocilpine Biol. Psychiatry 2009, 65, 1103-1106
    • (2009) Biol. Psychiatry , vol.65 , pp. 1103-1106
    • Hashimoto, K.1    Fujita, Y.2    Horio, M.3    Kunitachi, S.4    Iyo, M.5    Ferraris, D.6    Tsukamoto, T.7
  • 36
    • 70349770053 scopus 로고    scopus 로고
    • Effects of d-amino acid oxidase inhibitor on the extracellular d-alanine levels and the efficacy of d-alanine on dizocilpine-induced prepulse inhibition deficits in mice
    • Horio, M.; Fujita, Y.; Ishima, T.; Iyo, M.; Ferraris, D.; Tsukamoto, T.; Hashimoto, K. Effects of d-amino acid oxidase inhibitor on the extracellular d-alanine levels and the efficacy of d-alanine on dizocilpine-induced prepulse inhibition deficits in mice Open Clin. Chem. J. 2009, 2, 16-21
    • (2009) Open Clin. Chem. J. , vol.2 , pp. 16-21
    • Horio, M.1    Fujita, Y.2    Ishima, T.3    Iyo, M.4    Ferraris, D.5    Tsukamoto, T.6    Hashimoto, K.7
  • 37
    • 33751519528 scopus 로고    scopus 로고
    • 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
    • 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
    • (2006) Protein Sci. , vol.15 , pp. 2708-2717
    • Kawazoe, T.1    Tsuge, H.2    Pilone, M.S.3    Fukui, K.4
  • 39
    • 0031059866 scopus 로고    scopus 로고
    • Processing of X-ray diffraction data collected in oscillation mode
    • Abelson, J. N. Simon, M. I. Carter, C. W. Jr. Sweet, R. M. Academic Press: New York
    • Otwinowski, Z.; Minor, W. Processing of X-ray diffraction data collected in oscillation mode. In Methods in Enzymology; Abelson, J. N.; Simon, M. I.; Carter, C. W., Jr.; Sweet, R. M., Eds.; Academic Press: New York, 1997; Vol. 276, pp 307-326.
    • (1997) Methods in Enzymology , vol.276 , pp. 307-326
    • Otwinowski, Z.1    Minor, W.2
  • 40
    • 0028103275 scopus 로고
    • The CCP4 suite: Programs for protein crystallography
    • Collaborative Computational Project, N
    • Collaborative Computational Project, N. The CCP4 suite: programs for protein crystallography. Acta Crystallogr., Sect. D: Biol. Crystallogr. 1994, 50, 760-763.
    • (1994) Acta Crystallogr., Sect. D: Biol. Crystallogr. , vol.50 , pp. 760-763
  • 41
    • 33745637223 scopus 로고    scopus 로고
    • Automated ligand placement and refinement with a combined force field and shape potential
    • Wlodek, S.; Skillman, A. G.; Nicholls, A. Automated ligand placement and refinement with a combined force field and shape potential Acta Crystallogr., Sect. D: Biol. Crystallogr. 2006, 62, 741-749
    • (2006) Acta Crystallogr., Sect. D: Biol. Crystallogr. , vol.62 , pp. 741-749
    • Wlodek, S.1    Skillman, A.G.2    Nicholls, A.3
  • 43
    • 84962359573 scopus 로고    scopus 로고
    • High throughput artificial membrane permeability assay for blood-brain barrier
    • Di, L.; Kerns, E. H.; Fan, K.; McConnell, O. J.; Carter, G. T. High throughput artificial membrane permeability assay for blood-brain barrier Eur. J. Med. Chem. 2003, 38, 223-232
    • (2003) Eur. J. Med. Chem. , vol.38 , pp. 223-232
    • Di, L.1    Kerns, E.H.2    Fan, K.3    McConnell, O.J.4    Carter, G.T.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.