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Volumn 39, Issue 17, 1996, Pages 3248-3255

Synthesis and structure-activity relationships of 1,2,3,4- tetrahydroquinoline-2,3,4-trione 3-oximes: Novel and highly potent antagonists for NMDA receptor glycine site

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDROQUINOLINE DERIVATIVE; 5,7 DICHLOROKYNURENIC ACID; 6,7 DICHLORO 5 NITRO 2,3 QUINOXALINEDIONE; AMPA RECEPTOR; DIZOCILPINE; GLUTAMIC ACID; GLYCINE; GLYCINE RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; QUINOXALINE DERIVATIVE;

EID: 0000039703     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960214k     Document Type: Article
Times cited : (59)

References (37)
  • 1
    • 0023091647 scopus 로고
    • Glycine Potentiates the NMDA Response in Cultured Mouse Brain Neurons
    • Johnson, J. W.; Ascher, P. Glycine Potentiates the NMDA Response in Cultured Mouse Brain Neurons. Nature (London) 1987, 325, 529-531.
    • (1987) Nature (London) , vol.325 , pp. 529-531
    • Johnson, J.W.1    Ascher, P.2
  • 2
    • 0028872674 scopus 로고
    • Excitotoxicity and the NMDA Receptor - Still Lethal after Eight Years
    • Rothman, S. M.; Olney, J. W. Excitotoxicity and the NMDA Receptor - Still Lethal after Eight Years. Trends Neurosci. 1995, 18, 57-58.
    • (1995) Trends Neurosci. , vol.18 , pp. 57-58
    • Rothman, S.M.1    Olney, J.W.2
  • 3
    • 0029085982 scopus 로고
    • Excitatory Amino Acid Receptors and Neurodegeneration
    • Doble, A. Excitatory Amino Acid Receptors and Neurodegeneration. Therapie 1995, 50, 319-337.
    • (1995) Therapie , vol.50 , pp. 319-337
    • Doble, A.1
  • 4
    • 0025063609 scopus 로고
    • Excitatory Amino Acid Neurotoxicity and Neurodegenerative Disease
    • Meldrum, B.; Garthwaite, J. Excitatory Amino Acid Neurotoxicity and Neurodegenerative Disease. Trends Pharmacol. Sci. 1990, 11, 379-387.
    • (1990) Trends Pharmacol. Sci. , vol.11 , pp. 379-387
    • Meldrum, B.1    Garthwaite, J.2
  • 5
    • 0025762248 scopus 로고
    • Sites for Antagonism on the N-Methyl-D-aspartate Receptor Channel Complex
    • (a) Wong, E. H. F.; Kemp, J. A. Sites for Antagonism on the N-Methyl-D-aspartate Receptor Channel Complex. Annu. Rev. Pharmacol. Toxicol. 1991, 31, 401-425.
    • (1991) Annu. Rev. Pharmacol. Toxicol. , vol.31 , pp. 401-425
    • Wong, E.H.F.1    Kemp, J.A.2
  • 6
    • 0027241403 scopus 로고
    • Structural Requirements for the Development of Potent N-Methyl-D-aspartic Acid Receptor Antagonists
    • (b) Bigge, C. F. Structural Requirements for the Development of Potent N-Methyl-D-aspartic Acid Receptor Antagonists. Biochem. Pharmacol. 1993, 45, 1547-1561.
    • (1993) Biochem. Pharmacol. , vol.45 , pp. 1547-1561
    • Bigge, C.F.1
  • 7
    • 0001867791 scopus 로고
    • Glycine-Site N-Methyl-D-aspartate Receptor Antagonists
    • Kozikowski, A. P., Ed.; Raven Press: New York, Chapter 13
    • (a) Leeson, P. D. Glycine-Site N-Methyl-D-aspartate Receptor Antagonists. In Drug Design for Neuroscience; Kozikowski, A. P., Ed.; Raven Press: New York, 1993; Chapter 13.
    • (1993) Drug Design for Neuroscience
    • Leeson, P.D.1
  • 8
    • 0027469106 scopus 로고
    • The Glycine Site of the NMDA Receptor - Five Years on
    • (b) Kemp, J. A.; Leeson, P. D. The Glycine Site of the NMDA Receptor - Five Years on. Trends Pharmacol. Sci. 1993, 14, 20-25.
    • (1993) Trends Pharmacol. Sci. , vol.14 , pp. 20-25
    • Kemp, J.A.1    Leeson, P.D.2
  • 9
    • 0027988561 scopus 로고
    • The Glycine Site on the NMDA Receptor: Structure-Activity Relationships and Therapeutic Potential
    • Leeson, P. D.; Iversen, L. L. The Glycine Site on the NMDA Receptor: Structure-Activity Relationships and Therapeutic Potential. J. Med. Chem. 1994, 37, 4053-4067.
    • (1994) J. Med. Chem. , vol.37 , pp. 4053-4067
    • Leeson, P.D.1    Iversen, L.L.2
  • 10
    • 0027087308 scopus 로고
    • Competitive Antagonism of Glutamate Receptor Channels by Substituted Benzazepines in Cultured Cortical Neurons
    • Swartz, K. J.; Koroshetz, W. J.; Rees, A. H.; Huettner, J. E. Competitive Antagonism of Glutamate Receptor Channels by Substituted Benzazepines in Cultured Cortical Neurons. Mol. Pharmacol. 1992, 41, 1130-1141.
    • (1992) Mol. Pharmacol. , vol.41 , pp. 1130-1141
    • Swartz, K.J.1    Koroshetz, W.J.2    Rees, A.H.3    Huettner, J.E.4
  • 11
    • 0026779905 scopus 로고
    • 3-Phenyl-4-hydroxyquinoline-2(1H)-ones: Potent and Selective Antagonists at the Strychnine-Insensitive Glycine Site on the N-Methyl-D-aspartate Receptor Complex
    • McQuaid, L. A.; Smith, E. C. R.; Lodge, D.; Pralong, E.; Wikel, J. H.; Calligaro, D. O.; O'Malley, P. J. 3-Phenyl-4-hydroxyquinoline-2(1H)-ones: Potent and Selective Antagonists at the Strychnine-Insensitive Glycine Site on the N-Methyl-D-aspartate Receptor Complex. J. Med. Chem. 1992, 35, 3423-3425.
    • (1992) J. Med. Chem. , vol.35 , pp. 3423-3425
    • McQuaid, L.A.1    Smith, E.C.R.2    Lodge, D.3    Pralong, E.4    Wikel, J.H.5    Calligaro, D.O.6    O'Malley, P.J.7
  • 12
    • 0025740632 scopus 로고
    • Kynurenic Acid Derivatives. Structure-Activity Relationships for Excitatory Amino Acid Antagonism and Identification of Potent and Selective Antagonists at the Glycine Site on the N-Methyl-D-aspartate Receptor
    • Leeson, P. D.; Baker, R.; Carling, R. W.; Curtis, N. R.; Moore, K. W.; Williams, B. J.; Foster, A. C.; Donald, A. E.; Kemp, J. A.; Marshall, G. R. Kynurenic Acid Derivatives. Structure-Activity Relationships for Excitatory Amino Acid Antagonism and Identification of Potent and Selective Antagonists at the Glycine Site on the N-Methyl-D-aspartate Receptor. J. Med. Chem. 1991, 34, 1243-1252.
    • (1991) J. Med. Chem. , vol.34 , pp. 1243-1252
    • Leeson, P.D.1    Baker, R.2    Carling, R.W.3    Curtis, N.R.4    Moore, K.W.5    Williams, B.J.6    Foster, A.C.7    Donald, A.E.8    Kemp, J.A.9    Marshall, G.R.10
  • 13
    • 0026749637 scopus 로고
    • 2-Carboxytetrahydroquinolines. Conformational and Stereochemical Requirements for Antagonism of the Glycine Site on the NMDA Receptor
    • Carling, R. W.; Leeson, P. D.; Moseley, A. M.; Baker, R.; Foster, A. C.; Grimwood, S.; Kemp, J. A.; Marshall, G. R. 2-Carboxytetrahydroquinolines. Conformational and Stereochemical Requirements for Antagonism of the Glycine Site on the NMDA Receptor. J. Med. Chem. 1992, 35, 1942-1953.
    • (1992) J. Med. Chem. , vol.35 , pp. 1942-1953
    • Carling, R.W.1    Leeson, P.D.2    Moseley, A.M.3    Baker, R.4    Foster, A.C.5    Grimwood, S.6    Kemp, J.A.7    Marshall, G.R.8
  • 15
    • 0025766904 scopus 로고
    • Novel Indole-2-carboxylates as Ligands for the Strychnine-Insensitive N-Methyl-D-aspartate-Linked Glycine Receptor
    • Gray, N. M.; Dappen, M. S.; Cheng, B. K.; Cordi, A. A.; Biesterfeldt, J. P.; Hood, W. F.; Monahan, J. B. Novel Indole-2-carboxylates as Ligands for the Strychnine-Insensitive N-Methyl-D-aspartate-Linked Glycine Receptor. J. Med. Chem. 1991, 34, 1283-1292.
    • (1991) J. Med. Chem. , vol.34 , pp. 1283-1292
    • Gray, N.M.1    Dappen, M.S.2    Cheng, B.K.3    Cordi, A.A.4    Biesterfeldt, J.P.5    Hood, W.F.6    Monahan, J.B.7
  • 17
    • 0027973488 scopus 로고
    • Tricyclic Quinoxalinediones: 5,6-Dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-Dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones as Potent Antagonists for the Glycine Binding Site of the NMDA Receptor
    • Nagata, R.; Tanno, N.; Kodo, T.; Ae, N.; Yamaguchi, H.; Nishimura, T.; Antoku, F.; Tatsuno, T.; Kato, T.; Tanaka, Y.; Nakamura, M. Tricyclic Quinoxalinediones: 5,6-Dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-Dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones as Potent Antagonists for the Glycine Binding Site of the NMDA Receptor. J. Med. Chem. 1994, 37, 3956-3968.
    • (1994) J. Med. Chem. , vol.37 , pp. 3956-3968
    • Nagata, R.1    Tanno, N.2    Kodo, T.3    Ae, N.4    Yamaguchi, H.5    Nishimura, T.6    Antoku, F.7    Tatsuno, T.8    Kato, T.9    Tanaka, Y.10    Nakamura, M.11
  • 19
    • 0028862819 scopus 로고
    • Synthesis and Structure-Activity Relationships of Substituted 1,4-Dihydroquinoxaline-2,3-diones (QXs): Antagonists of the Glycine Site on the NMDA Receptor and of Non-NMDA Glutamate Receptors
    • Keana, J. F. W.; Kher, S. M.; Cai, S. X.; Dinsmore, C. M.; Glenn, A. G.; Guastella, J.; Huang, J. C.; Lu, Y.; Ilyin, V.; Lu, Y.; Mouser, P. L.; Woodward, R. M.; Weber, E. Synthesis and Structure-Activity Relationships of Substituted 1,4-Dihydroquinoxaline-2,3-diones (QXs): Antagonists of the Glycine Site on the NMDA Receptor and of Non-NMDA Glutamate Receptors. J. Med. Chem. 1995, 38, 4367-4379.
    • (1995) J. Med. Chem. , vol.38 , pp. 4367-4379
    • Keana, J.F.W.1    Kher, S.M.2    Cai, S.X.3    Dinsmore, C.M.4    Glenn, A.G.5    Guastella, J.6    Huang, J.C.7    Lu, Y.8    Ilyin, V.9    Lu, Y.10    Mouser, P.L.11    Woodward, R.M.12    Weber, E.13
  • 20
    • 10144231225 scopus 로고
    • Synthesis of 2,4-Dihydroxyquinolines Using Polyphosphoric Acid as the Cyclizing Agent
    • Patel, G. H.; Mehta, C. M. Synthesis of 2,4-Dihydroxyquinolines Using Polyphosphoric Acid as the Cyclizing Agent. J. Sci. Ind. Res. 1960,19B, 436-438.
    • (1960) J. Sci. Ind. Res. , vol.19 B , pp. 436-438
    • Patel, G.H.1    Mehta, C.M.2
  • 21
    • 84986492442 scopus 로고
    • Synthesis of Benzohalogenated 4-Hydroxy-2(1H)-quinolones
    • Kappe, T.; Karem, A. S.; Stadlbauer, W. Synthesis of Benzohalogenated 4-Hydroxy-2(1H)-quinolones. J. Heterocycl. Chem. 1988, 25, 857-862.
    • (1988) J. Heterocycl. Chem. , vol.25 , pp. 857-862
    • Kappe, T.1    Karem, A.S.2    Stadlbauer, W.3
  • 23
    • 84982077138 scopus 로고
    • On the 1,2-Shift of the Carboxyamido Group during the Benzylic Acid Rearrangement of Quinisatin
    • Dahn, H.; Donzel, A. On the 1,2-Shift of the Carboxyamido Group during the Benzylic Acid Rearrangement of Quinisatin. Helv. Chim. Acta 1967, 50, 1911-1917.
    • (1967) Helv. Chim. Acta , vol.50 , pp. 1911-1917
    • Dahn, H.1    Donzel, A.2
  • 24
    • 10144249420 scopus 로고
    • Formation and Photochemical Wolff Rearrangement of Cyclic α-Diazo Ketones: D-Norandrost-5-en-β9-ol-16-carboxylic Acids
    • Wiley: New York
    • Wheeler, T. N.; Meinwald, J. Formation and Photochemical Wolff Rearrangement of Cyclic α-Diazo Ketones: D-Norandrost-5-en-β9-ol-16-carboxylic Acids. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, pp 840-844.
    • (1988) Organic Syntheses , vol.6 COLLECT. VOL. , pp. 840-844
    • Wheeler, T.N.1    Meinwald, J.2
  • 25
    • 0026758827 scopus 로고
    • A Rapid Filtration Assay for the Glycine Binding Site on the NMDA Receptor in Rat Cortical Membranes Using [3H]Dichlorokynurenic Acid
    • Canton, T.; Doble, A.; Miquet, J.-M.; Jimonet, P.; Blanchard, J.-C. A Rapid Filtration Assay for the Glycine Binding Site on the NMDA Receptor in Rat Cortical Membranes Using [3H]Dichlorokynurenic Acid. J. Pharm. Pharmacol. 1992, 44, 812-816.
    • (1992) J. Pharm. Pharmacol. , vol.44 , pp. 812-816
    • Canton, T.1    Doble, A.2    Miquet, J.-M.3    Jimonet, P.4    Blanchard, J.-C.5
  • 26
    • 0029122075 scopus 로고
    • Synthesis of 1,4,7,8,9,10-Hexahydro-9-methyl-6-nitropyrido[3,4-f]-quinoxaline-2,3-dione and Related Quinoxalinedionea: Characterization of α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (and N-Methyl-D-aspartate) Receptor and Anticonvulsant Activity
    • Bigge, C. F.; Malone, T. C.; Boxer, P. A.; Nelson, C. B.; Ortwine, D. F.; Schelkun, R. M.; Retz, D. M.; Lescosky, L. J.; Borosky, S. A.; Vartanian, M. G.; Schwarz, R. D.; Campbell, G. W.; Robichaud, L. J.; Watjen, F. Synthesis of 1,4,7,8,9,10-Hexahydro-9-methyl-6-nitropyrido[3,4-f]-quinoxaline-2,3-dione and Related Quinoxalinedionea: Characterization of α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (and N-Methyl-D-aspartate) Receptor and Anticonvulsant Activity. J. Med. Chem. 1995, 38, 3720-3740.
    • (1995) J. Med. Chem. , vol.38 , pp. 3720-3740
    • Bigge, C.F.1    Malone, T.C.2    Boxer, P.A.3    Nelson, C.B.4    Ortwine, D.F.5    Schelkun, R.M.6    Retz, D.M.7    Lescosky, L.J.8    Borosky, S.A.9    Vartanian, M.G.10    Schwarz, R.D.11    Campbell, G.W.12    Robichaud, L.J.13    Watjen, F.14
  • 28
    • 0028916586 scopus 로고
    • In Vitro Pharmacology of ACEA-1021 and ACEA-1031: Systemically Active Quinoxalinediones with High Affinity and Selectivity for N-Methyl-D-aspartate Receptor Glycine Sites
    • Woodward, R. M.; Huettner, J. E.; Guastella, J.; Keana, J. F. W.; Weber, E. In Vitro Pharmacology of ACEA-1021 and ACEA-1031: Systemically Active Quinoxalinediones with High Affinity and Selectivity for N-Methyl-D-aspartate Receptor Glycine Sites. Mol. Pharmacol. 1995, 47, 568-581.
    • (1995) Mol. Pharmacol. , vol.47 , pp. 568-581
    • Woodward, R.M.1    Huettner, J.E.2    Guastella, J.3    Keana, J.F.W.4    Weber, E.5
  • 30
    • 0016767945 scopus 로고
    • 4-Hydroxy-3-nitro-2-quinolones and Related Compounds as Inhibitors of Allergic Reactions
    • Buckle, D. R.; Cantello, B. C. C.; Smith, H.; Spicer, B. A. 4-Hydroxy-3-nitro-2-quinolones and Related Compounds as Inhibitors of Allergic Reactions. J. Med. Chem. 1975, 18, 726-732.
    • (1975) J. Med. Chem. , vol.18 , pp. 726-732
    • Buckle, D.R.1    Cantello, B.C.C.2    Smith, H.3    Spicer, B.A.4
  • 31
    • 10144224727 scopus 로고
    • Fluorinated Organic Pigments. III. Preparation of 5,6,7,8-Tetrafluoro-2,4-quinolinediol and Some Azo Colors Derived Therefrom
    • Tanabe, T.; Ishikawa, N. Fluorinated Organic Pigments. III. Preparation of 5,6,7,8-Tetrafluoro-2,4-quinolinediol and Some Azo Colors Derived Therefrom. Nippon Kagaku Kaishi 1972, 8, 1255; CA 77:141464.
    • (1972) Nippon Kagaku Kaishi , vol.8 , pp. 1255
    • Tanabe, T.1    Ishikawa, N.2
  • 32
    • 10144234608 scopus 로고    scopus 로고
    • Tanabe, T.; Ishikawa, N. Fluorinated Organic Pigments. III. Preparation of 5,6,7,8-Tetrafluoro-2,4-quinolinediol and Some Azo Colors Derived Therefrom. Nippon Kagaku Kaishi 1972, 8, 1255; CA 77:141464.
    • CA , vol.77 , pp. 141464
  • 34
    • 0026377665 scopus 로고
    • Synthesis of Certain Sulphonamides and Aminopyranoquinoline Derivatives from 4-Hydroxyquinoline with Biological Interest
    • Fadda, A. A.; Khalil, A. M.; El-Habbal, M. M. Synthesis of Certain Sulphonamides and Aminopyranoquinoline Derivatives from 4-Hydroxyquinoline with Biological Interest. J. Indian Chem. Soc. 1991, 68, 393-395.
    • (1991) J. Indian Chem. Soc. , vol.68 , pp. 393-395
    • Fadda, A.A.1    Khalil, A.M.2    El-Habbal, M.M.3
  • 35
    • 0017613512 scopus 로고
    • A Simplification of the Protein Assay Method of Lowry et al. Which Is More Generally Applicable
    • Peterson, G. L. A Simplification of the Protein Assay Method of Lowry et al. Which Is More Generally Applicable. Anal. Biochem. 1977, 83, 346-356.
    • (1977) Anal. Biochem. , vol.83 , pp. 346-356
    • Peterson, G.L.1
  • 37
    • 0027522536 scopus 로고
    • Further Concerns over Cheng-Prusoff Analysis
    • Leff, P.; Dougall, I. G. Further Concerns over Cheng-Prusoff Analysis. Trends Pharmacol. Sci. 1993, 14, 110-112.
    • (1993) Trends Pharmacol. Sci. , vol.14 , pp. 110-112
    • Leff, P.1    Dougall, I.G.2


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