메뉴 건너뛰기




Volumn 47, Issue 27, 2004, Pages 6948-6957

Bioisosteric modifications of 2-arylureidobenzoic acids: Selective noncompetitive antagonists for the homomeric kainate receptor subtype GluR5

Author keywords

[No Author keywords available]

Indexed keywords

1 (3 BROMOPHENYL) 3 [5 CHLORO 2(1H) TETRAZOL 5 YLPHENYL]UREA; 2 [3 (3 BROMOPHENYL)UREIDO] 4 CHLOROBENZENESULFONIC ACID; ALPHA AMINO 5 TERT BUTYL 3 HYDROXY 4 ISOXAZOLEPROPIONIC ACID; GLUTAMATE RECEPTOR; GLUTAMATE RECEPTOR 5; GLUTAMATE RECEPTOR AGONIST; GLUTAMATE RECEPTOR ANTAGONIST; KAINIC ACID RECEPTOR; RECEPTOR SUBTYPE; TRITIUM; UNCLASSIFIED DRUG; UREIDOBENZOIC ACID DERIVATIVE;

EID: 11244334171     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030638w     Document Type: Article
Times cited : (45)

References (34)
  • 3
    • 0034059343 scopus 로고    scopus 로고
    • Pharmacology of AMPA/kainate receptor ligands and their therapeutic potential in neurological and psychiatric disorders
    • Lee, G. J. Pharmacology of AMPA/kainate receptor ligands and their therapeutic potential in neurological and psychiatric disorders. Drugs 2000, 59, 33-78.
    • (2000) Drugs , vol.59 , pp. 33-78
    • Lee, G.J.1
  • 4
    • 0032467053 scopus 로고    scopus 로고
    • Glutamate in CNS disorders as a target for drug development: An update
    • Parsons, C. G.; Danysz, W.; Quack, G. Glutamate in CNS disorders as a target for drug development: An update. Drug News Perspect. 1998, 11, 523-569.
    • (1998) Drug News Perspect. , vol.11 , pp. 523-569
    • Parsons, C.G.1    Danysz, W.2    Quack, G.3
  • 5
    • 0032191984 scopus 로고    scopus 로고
    • Decahydroisoquinolines: Novel competitive AMPA/kainate antagonists with neuroprotective effects in global cerebral ischaemia
    • O'Neill, M. J.; Bond, A.; Ornstein, P. L.; Ward, M. A.; Hicks, C. A.; Hoo, K.; Bleakman, D.; Lodge, D. Decahydroisoquinolines: novel competitive AMPA/kainate antagonists with neuroprotective effects in global cerebral ischaemia. Neuropharmacology 1998, 37, 1211-1222.
    • (1998) Neuropharmacology , vol.37 , pp. 1211-1222
    • O'Neill, M.J.1    Bond, A.2    Ornstein, P.L.3    Ward, M.A.4    Hicks, C.A.5    Hoo, K.6    Bleakman, D.7    Lodge, D.8
  • 7
    • 0031862305 scopus 로고    scopus 로고
    • Kainate GluR5 receptor subtype mediates the nociceptive response to formalin in the rat
    • Simmons, R. M.; Li, D. L.; Hoo, K. H.; Deverill, M.; Ornstein, P. L.; Iyengar, S. Kainate GluR5 receptor subtype mediates the nociceptive response to formalin in the rat. Neuropharmacology 1998, 37, 25-36.
    • (1998) Neuropharmacology , vol.37 , pp. 25-36
    • Simmons, R.M.1    Li, D.L.2    Hoo, K.H.3    Deverill, M.4    Ornstein, P.L.5    Iyengar, S.6
  • 10
    • 0346365496 scopus 로고    scopus 로고
    • 2-Arylureidobenzoic acids: Selective noncompetitive antagonists for the homomeric kainate receptor subtype GluR5
    • Valgeirsson, J.; Nielsen, E. Ø.; Peters, D.; Varming, T.; Mathiesen, C.; Kristensen, A. S.; Madsen, U. 2-Arylureidobenzoic acids: selective noncompetitive antagonists for the homomeric kainate receptor subtype GluR5. J. Med. Chem. 2003, 46, 5834-5843.
    • (2003) J. Med. Chem. , vol.46 , pp. 5834-5843
    • Valgeirsson, J.1    Nielsen, E.Ø.2    Peters, D.3    Varming, T.4    Mathiesen, C.5    Kristensen, A.S.6    Madsen, U.7
  • 11
    • 0039781398 scopus 로고
    • An interesting chloride ion effect in the Heck reaction
    • Merlic, C. A.; Semmelhack, M. F. An interesting chloride ion effect in the Heck reaction. J. Organomet. Chem. 1990, 391, C23-C27.
    • (1990) J. Organomet. Chem. , vol.391
    • Merlic, C.A.1    Semmelhack, M.F.2
  • 12
    • 0035807527 scopus 로고    scopus 로고
    • Highly satisfactory procedures for the Pd-catalyzed cross coupling of aryl electrophiles with in situ generated alkynylzinc derivatives
    • Anastasia, L.; Negishi, E. Highly satisfactory procedures for the Pd-catalyzed cross coupling of aryl electrophiles with in situ generated alkynylzinc derivatives. Org. Lett. 2001, 3, 3111-3114.
    • (2001) Org. Lett. , vol.3 , pp. 3111-3114
    • Anastasia, L.1    Negishi, E.2
  • 13
    • 11244286291 scopus 로고
    • o-Toluidinsulfonic acid
    • Allen van, A. o-Toluidinsulfonic acid. Org. Synth. 1927, 27, 88.
    • (1927) Org. Synth. , vol.27 , pp. 88
    • Van Allen, A.1
  • 14
    • 0031799295 scopus 로고    scopus 로고
    • Novel synthesis of 5-substituted tetrazoles from nitriles
    • Koguro, K.; Oga, T.; Mitsui, S.; Orita, R. Novel synthesis of 5-substituted tetrazoles from nitriles. Synthesis 1998, 910-914.
    • (1998) Synthesis , pp. 910-914
    • Koguro, K.1    Oga, T.2    Mitsui, S.3    Orita, R.4
  • 15
    • 0034742757 scopus 로고    scopus 로고
    • Binding interactions between 3-aryl-1,2,4-oxadiazol-5-ones and a trisimidazoline base
    • Reichert, A.; Froehlich, R.; Ferguson, R.; Kraft, A. Binding interactions between 3-aryl-1,2,4-oxadiazol-5-ones and a trisimidazoline base. J. Chem. Soc., Perkin Trans. 1 2001, 1321-1328.
    • (2001) J. Chem. Soc., Perkin Trans. 1 , pp. 1321-1328
    • Reichert, A.1    Froehlich, R.2    Ferguson, R.3    Kraft, A.4
  • 16
    • 0029058842 scopus 로고
    • Studies of the cyclocondensation of o-aminophenyl-substituted ketoximes and amidoximes with carbonyl compounds giving quinazoline derivatives
    • Lessel, J. Studies of the cyclocondensation of o-aminophenyl-substituted ketoximes and amidoximes with carbonyl compounds giving quinazoline derivatives. Arch. Pharm. (Weinheim, Ger.) 1995, 328, 397-402.
    • (1995) Arch. Pharm. (Weinheim, Ger.) , vol.328 , pp. 397-402
    • Lessel, J.1
  • 17
    • 8044238468 scopus 로고
    • Synthesis of dis-disalicylide and of flavones containing a chromeno[4,3-B]chromen nucleus
    • Dean, F. M.; Small, S.; Hindley, K. B. Synthesis of dis-disalicylide and of flavones containing a chromeno[4,3-B]chromen nucleus. J. Chem. Soc., Perkin Trans. 1 1972, 16, 2007-2010.
    • (1972) J. Chem. Soc., Perkin Trans. 1 , vol.16 , pp. 2007-2010
    • Dean, F.M.1    Small, S.2    Hindley, K.B.3
  • 18
    • 0036836947 scopus 로고    scopus 로고
    • 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: Medicinal chemistry and synthetic methods
    • Herr, R. J. 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods. Bioorg. Med. Chem. 2002, 10, 3379-3393.
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 3379-3393
    • Herr, R.J.1
  • 19
    • 0030480485 scopus 로고    scopus 로고
    • Synthesis and angiotensin II receptor antagonistic activities of benzimidazole derivatives bearing acidic heterocycles as novel tetrazole bioisosteres
    • Kohara, Y.; Kubo, K.; Imamiya, E.; Wada, T.; Inada, Y.; Naka, T. Synthesis and angiotensin II receptor antagonistic activities of benzimidazole derivatives bearing acidic heterocycles as novel tetrazole bioisosteres. J. Med. Chem. 1996, 39, 5228-5235.
    • (1996) J. Med. Chem. , vol.39 , pp. 5228-5235
    • Kohara, Y.1    Kubo, K.2    Imamiya, E.3    Wada, T.4    Inada, Y.5    Naka, T.6
  • 20
    • 0035667885 scopus 로고    scopus 로고
    • Stereoselective synthesis of (E)-3-(methoxycarbonyl)methylene-1,3- dihydroindol-2-ones by palladium-catalyzed oxidative carbonylation of 2-ethynylanilines
    • Gabriele, B.; Salerno, G.; Veltri, L.; Costa, M.; Massera, C. Stereoselective synthesis of (E)-3-(methoxycarbonyl)methylene-1,3-dihydroindol- 2-ones by palladium-catalyzed oxidative carbonylation of 2-ethynylanilines. Eur. J. Org. Chem. 2001, 24, 4607-4613.
    • (2001) Eur. J. Org. Chem. , vol.24 , pp. 4607-4613
    • Gabriele, B.1    Salerno, G.2    Veltri, L.3    Costa, M.4    Massera, C.5
  • 21
    • 0033838318 scopus 로고    scopus 로고
    • Straight-forward synthesis of new tetrahydroquinoline derivatives
    • Di Fabio, R.; Alvaro, G.; Bertani, B.; Giacobbe, S. Straight-forward synthesis of new tetrahydroquinoline derivatives. Can. J. Chem. 2000, 78, 809-815.
    • (2000) Can. J. Chem. , vol.78 , pp. 809-815
    • Di Fabio, R.1    Alvaro, G.2    Bertani, B.3    Giacobbe, S.4
  • 22
  • 24
    • 84982336140 scopus 로고
    • Sulfonsäurederivate mehrfach substituierter benzole und ihre biologische aktivität
    • Logemann, W.; Giraldi, P.; Galimberti, S. Sulfonsäurederivate mehrfach substituierter benzole und ihre biologische aktivität (Substituted benzene sulfonic acid derivatives and their biological activities). Justus Liebigs Ann. Chem. 1959, 623, 157-165.
    • (1959) Justus Liebigs Ann. Chem. , vol.623 , pp. 157-165
    • Logemann, W.1    Giraldi, P.2    Galimberti, S.3
  • 25
    • 0021262896 scopus 로고
    • Hypolipidemic activity of phthalimide derivatives. 7. Structure-activity studies of indazolone analogs
    • Wyrick, S. D.; Voorstad, P. J.; Cocolas, G.; Hall, I. H. Hypolipidemic activity of phthalimide derivatives. 7. Structure-activity studies of indazolone analogs. J. Med. Chem. 1984, 27, 768-772.
    • (1984) J. Med. Chem. , vol.27 , pp. 768-772
    • Wyrick, S.D.1    Voorstad, P.J.2    Cocolas, G.3    Hall, I.H.4
  • 26
    • 11244289554 scopus 로고
    • Cinnolines. III. Attempted syntheses of the cinnoline nucleus
    • Leonard, N. J.; Boyd, S. N., Jr.; Herbrandson, H. F. Cinnolines. III. Attempted syntheses of the cinnoline nucleus. J. Org. Chem. 1947, 12, 47-56.
    • (1947) J. Org. Chem. , vol.12 , pp. 47-56
    • Leonard, N.J.1    Boyd Jr., S.N.2    Herbrandson, H.F.3
  • 27
    • 0009590388 scopus 로고    scopus 로고
    • Optimization of isatine oximes as neuroprotective AMPA receptor antagonists: In vitro and in vivo evaluation of SPD 502
    • Turski, L., Schoepp, D. D., Cavalheiro, E. A., Eds.; IOS Press: Amsterdam
    • Vanning, T.; Ahring, P. K.; Sager, T. N.; Johansen, T. H.; Wätjen, F.; Drejer, J. Optimization of isatine oximes as neuroprotective AMPA receptor antagonists: in vitro and in vivo evaluation of SPD 502. In Excitatory Amino Acids: Ten Years Later; Turski, L., Schoepp, D. D., Cavalheiro, E. A., Eds.; IOS Press: Amsterdam, 2001; pp 193-195.
    • (2001) Excitatory Amino Acids: Ten Years Later , pp. 193-195
    • Vanning, T.1    Ahring, P.K.2    Sager, T.N.3    Johansen, T.H.4    Wätjen, F.5    Drejer, J.6
  • 28
    • 0036077331 scopus 로고    scopus 로고
    • Correlation between anti-convulsant activity and inhibitory action on glial gamma-aminobutyric acid uptake of the highly selective mouse gamma-aminobutyric acid transporter 1 inhibitor 3-hydroxy-4-amino-4,5,6,7- tetrahydro-1,2-benzisoxazole and its N-alkylated analogs
    • White, H. S.; Sarup, A.; Bolvig, T.; Kristensen, A. S.; Petersen, G.; Nelson, N.; Pickering, D. S.; Larsson, O. M.; Frølund, B.; Krogsgaard-Larsen, P.; Schousboe, A. Correlation between anti-convulsant activity and inhibitory action on glial gamma-aminobutyric acid uptake of the highly selective mouse gamma-aminobutyric acid transporter 1 inhibitor 3-hydroxy-4-amino-4,5,6,7-tetrahydro-1,2-benzisoxazole and its N-alkylated analogs. J. Pharmacol. Exp. Ther. 2002, 302, 636-644.
    • (2002) J. Pharmacol. Exp. Ther. , vol.302 , pp. 636-644
    • White, H.S.1    Sarup, A.2    Bolvig, T.3    Kristensen, A.S.4    Petersen, G.5    Nelson, N.6    Pickering, D.S.7    Larsson, O.M.8    Frølund, B.9    Krogsgaard-Larsen, P.10    Schousboe, A.11
  • 30
    • 0026563864 scopus 로고
    • Relief of experimental spasticity and anxiolytic/anticonvulsant actions of the alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate antagonist 2,3-dihydroxy-6-nitro-7-sulfamoyl-benzo(F)quinoxaline
    • Turski, L.; Jacobsen, P.; Honore, T.; Stephens, D. N. Relief of experimental spasticity and anxiolytic/anticonvulsant actions of the alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate antagonist 2,3-dihydroxy-6-nitro-7-sulfamoyl-benzo(F)quinoxaline. J. Pharmacol. Exp. Ther. 1992, 260, 742-747.
    • (1992) J. Pharmacol. Exp. Ther. , vol.260 , pp. 742-747
    • Turski, L.1    Jacobsen, P.2    Honore, T.3    Stephens, D.N.4
  • 33
    • 0028865828 scopus 로고
    • (3SR,4aRS,6SR,8aRS)-6-(1H-tetrazol-5-yl)decahydroisoquinoline-3- carboxylic acid, a novel, competitive, systemically active NMDA and AMPA receptor antagonist
    • Ornstein, P. L.; Arnold, M. B.; Allen, N. K.; Leander, J. D.; Tizzano, J. P.; Lodge, D.; Schoepp, D. D. (3SR,4aRS,6SR,8aRS)-6-(1H-tetrazol-5-yl) decahydroisoquinoline-3-carboxylic acid, a novel, competitive, systemically active NMDA and AMPA receptor antagonist. J. Med. Chem. 1995, 38, 4885-4890.
    • (1995) J. Med. Chem. , vol.38 , pp. 4885-4890
    • Ornstein, P.L.1    Arnold, M.B.2    Allen, N.K.3    Leander, J.D.4    Tizzano, J.P.5    Lodge, D.6    Schoepp, D.D.7
  • 34
    • 0029946631 scopus 로고    scopus 로고
    • Structure-activity studies of 6-substituted decahydroisoquinoline-3- carboxylic acid AMPA receptor antagonists. 2. Effects of distal acid bioisosteric substitution, absolute stereochemical preferences, and in vivo activity
    • Ornstein, P. L.; Arnold, M. B.; Allen, N. K; Bleisch, T.; Borromeo, P. S.; Lugar, C. W.; Leander, J. D.; Lodge, D.; Schoepp, D. D. Structure-activity studies of 6-substituted decahydroisoquinoline-3-carboxylic acid AMPA receptor antagonists. 2. Effects of distal acid bioisosteric substitution, absolute stereochemical preferences, and in vivo activity. J. Med. Chem. 1996, 39, 2232-2244.
    • (1996) J. Med. Chem. , vol.39 , pp. 2232-2244
    • Ornstein, P.L.1    Arnold, M.B.2    Allen, N.K.3    Bleisch, T.4    Borromeo, P.S.5    Lugar, C.W.6    Leander, J.D.7    Lodge, D.8    Schoepp, D.D.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.