메뉴 건너뛰기




Volumn 36, Issue 22, 1993, Pages 3386-3396

3-Acyl-4-hydroxyquinolin-2(1H)-ones. Systemically Active Anticonvulsants Acting by Antagonism at the Glycine Site of the N-Methyl-d-Aspartate Receptor Complex

Author keywords

[No Author keywords available]

Indexed keywords

5,7 DICHLORO 1,2,3,4 TETRAHYDRO 4 (3 PHENYLUREIDO) 2 QUINOLINECARBOXYLIC ACID; 7 CHLORO 3 (CYCLOPROPYLCARBONYL) 4 HYDROXY 2(1H) QUINOLONE; 7 CHLORO 4 HYDROXY 2(1H) OXO 3 QUINOLINECARBOXYLIC ACID 3 (3 HYDROXYPHENYL) 2 PROPYNYL ESTER; DRUG CARRIER; EXCITATORY AMINO ACID RECEPTOR; GLYCINE; L 701252; L 701273; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0027331480     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00074a020     Document Type: Article
Times cited : (101)

References (46)
  • 1
    • 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
  • 2
  • 3
    • 0025390880 scopus 로고
    • Protection against ischaemic neuronal damage by drugs acting on excitatory neurotransmission
    • Meldrum, B. Protection against ischaemic neuronal damage by drugs acting on excitatory neurotransmission. Cerebrovasc. Brain Metab. Rev. 1990, 2, 27–57.
    • (1990) Cerebrovasc. Brain Metab. Rev. , vol.2 , pp. 27-57
    • Meldrum, B.1
  • 4
    • 0024363934 scopus 로고
    • Excitatory amino acids and Alzheimers disease
    • Greenamyre, J. T.; Young, A. B. Excitatory amino acids and Alzheimers disease. Neurobiol. of Aging 1989, 10, 593–603.
    • (1989) Neurobiol. of Aging , vol.10 , pp. 593-603
    • Greenamyre, J.T.1    Young, A.B.2
  • 5
    • 0026569410 scopus 로고
    • Models of neuronal injury in AIDS: another role for the NMDA receptor?
    • Lipton, S. A. Models of neuronal injury in AIDS: another role for the NMDA receptor? Trends Neurosci. 1992, 15, 75–79.
    • (1992) Trends Neurosci. , vol.15 , pp. 75-79
    • Lipton, S.A.1
  • 7
    • 0025191432 scopus 로고
    • Structure-activity relationships in the development of excitatory amino acid receptor agonists and competitive antagonists
    • Watkins, J. C.; Krogsgaard-Larsen, P.; Honoré, T. Structure-activity relationships in the development of excitatory amino acid receptor agonists and competitive antagonists. Trends Pharmacol. Sci. 1990, 11, 25–33.
    • (1990) Trends Pharmacol. Sci. , vol.11 , pp. 25-33
    • Watkins, J.C.1    Krogsgaard-Larsen, P.2    Honoré, T.3
  • 9
    • 0023820777 scopus 로고
    • 8H]-MK-801 binding to the N-methyl-D-aspartate receptor-ion channel complex by L-glutamate, glycine, and polyamines
    • 8H]-MK-801 binding to the N-methyl-D-aspartate receptor-ion channel complex by L-glutamate, glycine, and polyamines. J. Neurochem. 1988, 51, 830–836.
    • (1988) J. Neurochem. , vol.51 , pp. 830-836
    • Ransom, R.W.1    Stec, N.L.2
  • 10
    • 0024321139 scopus 로고
    • Ifenprodil and SL 82.0715 are antagonists at the polyamine site of the N-methyl-D-aspartate (NMDA) receptor
    • Carter, C.; Rivy, J.-P.; Scatton, B. Ifenprodil and SL 82.0715 are antagonists at the polyamine site of the N-methyl-D-aspartate (NMDA) receptor. Eur. J. Pharmacol. 1989, 164, 611–612.
    • (1989) Eur. J. Pharmacol. , vol.164 , pp. 611-612
    • Carter, C.1    Rivy, J.-P.2    Scatton, B.3
  • 11
    • 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 1987, 325, 529–531.
    • (1987) Nature , vol.325 , pp. 529-531
    • Johnson, J.W.1    Ascher, P.2
  • 12
    • 0023754192 scopus 로고
    • Requirement for glycine in activation of NMDA-receptors expressed in Xenopus oocytes
    • Kleckner, D. W.; Dingledine, R. Requirement for glycine in activation of NMDA-receptors expressed in Xenopus oocytes. Science 1988, 241, 835–837.
    • (1988) Science , vol.241 , pp. 835-837
    • Kleckner, D.W.1    Dingledine, R.2
  • 13
    • 0027469106 scopus 로고
    • The glycine site on the NMDA receptor - five years on
    • Kemp, J. A.; Leeson P. D. The glycine site on 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
  • 14
    • 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
  • 15
    • 0027439407 scopus 로고
    • Anticonvulsant activity of glycine-site NMDA antagonists—I.2-Carboxyl prodrugs of 5,7-dichlorokynurenic acid
    • Moore, K. W.; Leeson, P. D.; Carling, R. W.; Tricklebank, M. D.; Singh, L. Anticonvulsant activity of glycine-site NMDA antagonists—I.2-Carboxyl prodrugs of 5,7-dichlorokynurenic acid. Bioorg. Med. Chem. Lett. 1993, 3, 61–64.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 61-64
    • Moore, K.W.1    Leeson, P.D.2    Carling, R.W.3    Tricklebank, M.D.4    Singh, L.5
  • 16
    • 0025242947 scopus 로고
    • 4-[(Carboxymethyl)oxy]-and 4-[Carboxymethyl)amino]-5,7-dichloroquinoline-2-carboxync acid: New antagonists of the strychnine-insensitive glycine binding site on the N-methyl-D-aspartate receptor complex
    • Harrison, B. L.; Baron, B. M.; Cousino, D. M.; McDonald, I. A. 4-[(Carboxymethyl)oxy]-and 4-[Carboxymethyl)amino]-5,7-dichloroquinoline-2-carboxync acid: New antagonists of the strychnine-insensitive glycine binding site on the N-methyl-D-aspartate receptor complex. J. Med. Chem. 1990, 33, 3130–3132.
    • (1990) J. Med. Chem. , vol.33 , pp. 3130-3132
    • Harrison, B.L.1    Baron, B.M.2    Cousino, D.M.3    McDonald, I.A.4
  • 17
    • 0026749637 scopus 로고
    • 2-Carboxytet-rahydroquinolines. Conformational and stereochemical requirements for antagonism on the glycine site of 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-Carboxytet-rahydroquinolines. Conformational and stereochemical requirements for antagonism on the glycine site of 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
  • 20
    • 0025027922 scopus 로고
    • 3-(2-Carboxyindol-3-yl)propionic acid derivatives: antagonists of the strychnine insensitive glycine receptor associated with the N-methyl-D-aspartate receptor complex
    • Salituro, F. G.; Harrison, B. L.; Baron, B. M.; Nyce, P. L.; Stewart, K. T.; Kenne, J. H.; White, H. S.; McDonald, I. A. 3-(2-Carboxyindol-3-yl)propionic acid derivatives: antagonists of the strychnine insensitive glycine receptor associated with the N-methyl-D-aspartate receptor complex. J. Med. Chem. 1990, 33, 2944–2946.
    • (1990) J. Med. Chem. , vol.33 , pp. 2944-2946
  • 22
    • 0026745933 scopus 로고
    • 2-Carboxy indolines and indoles as potential glycine/NMDA antagonists: effect of five-membered ring conformation on affinity
    • Rowley, M.; Leeson, P. D.; Grimwood, S.; Foster, A.; Saywell, K. 2-Carboxy indolines and indoles as potential glycine/NMDA antagonists: effect of five-membered ring conformation on affinity. Bioorg. Med. Chem. Lett. 1992, 2, 1627–1630.
    • (1992) Bioorg. Med. Chem. Lett. , vol.2 , pp. 1627-1630
    • Rowley, M.1    Leeson, P.D.2    Grimwood, S.3    Foster, A.4    Saywell, K.5
  • 24
    • 0026532928 scopus 로고
    • Quinoxaline derivatives: Structure-activity relationships and physiological implications of inhibition of N-methyl-D-aspartate and non-N-methyl-D-aspartate receptor mediated currents and synaptic potentials
    • Randle, J. C. R.; Guet, T.; Bobichon, C.; Moreau, C.; Curutchet, P.; Lambolez, B.; de Carvalho, L. P.; Cordi, A.; Lepagnol, J. M. Quinoxaline derivatives: Structure-activity relationships and physiological implications of inhibition of N-methyl-D-aspartate and non-N-methyl-D-aspartate receptor mediated currents and synaptic potentials. Mol. Pharmacol. 1992, 41, 337–345.
    • (1992) Mol. Pharmacol. , vol.41 , pp. 337-345
    • Randle, J.C.R.1    Guet, T.2    Bobichon, C.3    Moreau, C.4    Curutchet, P.5    Lambolez, B.6    de Carvalho, L.P.7    Cordi, A.8    Lepagnol, J.M.9
  • 25
    • 0026579124 scopus 로고
    • Competitive inhibition by NBQX of kainate/AMPA receptor currents and excitatory synaptic potentials: importance of 6-nitro substitution
    • Randle J. C. R.; Guet, T.; Cordi, A.; Lepagnol, J. M. Competitive inhibition by NBQX of kainate/AMPA receptor currents and excitatory synaptic potentials: importance of 6-nitro substitution. Eur. J. Pharmacol. 1992, 215, 237–244.
    • (1992) Eur. J. Pharmacol. , vol.215 , pp. 237-244
    • Randle, J.C.R.1    Guet, T.2    Cordi, A.3    Lepagnol, J.M.4
  • 27
    • 0026545425 scopus 로고
    • Routes to 4-substituted analogues of the glycine/NMDA antagonist HA-966. Enantioselective synthesis of (3R, 4R) 3-amino-1-hydroxy-4-methyl-2-pyrrolidinone (L-687,414)
    • Rowley, M.; Leeson, P. D.; Wilhams, B. J.; Moore, K. W.; Baker, R. Routes to 4-substituted analogues of the glycine/NMDA antagonist HA-966. Enantioselective synthesis of (3R, 4R) 3-amino-1-hydroxy-4-methyl-2-pyrrolidinone (L-687,414) Tetrahedron 1992, 48, 3557–3570.
    • (1992) Tetrahedron , vol.48 , pp. 3557-3570
    • Rowley, M.1    Leeson, P.D.2    Wilhams, B.J.3    Moore, K.W.4    Baker, R.5
  • 28
    • 0000769254 scopus 로고
    • Neuroprotective effects of the glycine site antagonist (+)cis-4-methyl-HA-966 (L-687,414) in a rat focal ischaemia model
    • Gill, R.; Hargreaves, R.; Kemp, J. A. Neuroprotective effects of the glycine site antagonist (+)cis-4-methyl-HA-966 (L-687,414) in a rat focal ischaemia model. J. Cereb. Blood Flow Metab. 1991, 11 (Suppl. 2), S304.
    • (1991) J. Cereb. Blood Flow Metab. , vol.11 , pp. S304
    • Gill, R.1    Hargreaves, R.2    Kemp, J.A.3
  • 30
    • 0026779905 scopus 로고
    • 3-Phenyl-4-hydroxyquinolin-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-hydroxyquinolin-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
  • 34
    • 0021686627 scopus 로고
    • Synthesis of 3-oxo-3,4-dihydro-2H-l,4-benzoxazines and -1,4-benzothiazines under phase-transfer catalysis
    • Huang, X.; Chan, C.-C. Synthesis of 3-oxo-3,4-dihydro-2H-l,4-benzoxazines and -1,4-benzothiazines under phase-transfer catalysis. Synthesis 1984, 851–852.
    • (1984) Synthesis , pp. 851-852
    • Huang, X.1    Chan, C.-C.2
  • 36
    • 0003119165 scopus 로고
    • A comparison of the agonist-dependency of the block produced by uncompetitive NMDA antagonists on rat cortical slices
    • Kemp, J. A.; Marshall, G. R.; Priestley, T. A comparison of the agonist-dependency of the block produced by uncompetitive NMDA antagonists on rat cortical slices. Mol. Neuropharm. 1991, 1, 66–70.
    • (1991) Mol. Neuropharm. , vol.1 , pp. 66-70
    • Kemp, J.A.1    Marshall, G.R.2    Priestley, T.3
  • 37
  • 38
    • 0024323992 scopus 로고
    • The behavioural effects of MK-801: a comparison with antagonists acting non-competitively and competitively at the NMDA receptor
    • Tricklebank, M. D.; Singh, L.; Oies, R. J.; Preston, C.; Iversen S. D. The behavioural effects of MK-801: a comparison with antagonists acting non-competitively and competitively at the NMDA receptor. Eur. J. Pharmacol. 1989, 167, 127–135.
    • (1989) Eur. J. Pharmacol. , vol.167 , pp. 127-135
    • Tricklebank, M.D.1    Singh, L.2    Oies, R.J.3    Preston, C.4    Iversen, S.D.5
  • 43
    • 33845377147 scopus 로고
    • + - r complexes of onium ions with olefins and benzene derivatives
    • (Mautner)
    • + - r complexes of onium ions with olefins and benzene derivatives. J. Am. Chem. Soc. 1985, 107, 474–479.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 474-479
    • Deakne, C.A.1    Meot-Ner, M.2
  • 45
    • 85022712979 scopus 로고
    • Barton, D., Ollis, W. D., Eds; Pergamon Press: Oxford
    • Sutherland, I. O. Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds; Pergamon Press: Oxford, 1979; Vol. 2, pp 1040–1041.
    • (1979) Comprehensive Organic Chemistry , vol.2 , pp. 1040-1041
    • Sutherland, I.O.1
  • 46
    • 0000234475 scopus 로고
    • Simultaneous determination of electronic and lipophilic properties [pK., P(ion), P(neutral)] of acids and bases by nonlinear regression analysis of pH-dependent partition measurements
    • Schaper, K.-J. Simultaneous determination of electronic and lipophilic properties [pK., P(ion), P(neutral)] of acids and bases by nonlinear regression analysis of pH-dependent partition measurements. J. Chem. Res. (5) 1979, 357.
    • (1979) J. Chem. Res. , vol.5 , pp. 357
    • Schaper, K.-J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.