메뉴 건너뛰기




Volumn 54, Issue 13, 2011, Pages 4793-4805

Selective kainate receptor (GluK1) ligands structurally based upon 1H-cyclopentapyrimidin-2,4(1 H,3 H)-dione: Synthesis, molecular modeling, and pharmacological and biostructural characterization

Author keywords

[No Author keywords available]

Indexed keywords

1 (2' AMINO 2' CARBOXYETHYL) 1,2,3,4,5,6,7,8 OCTAHYDROBENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2,4 DIONE; 1 (2' AMINO 2' CARBOXYETHYL) 3 [(2 CARBOXYTHIEN 3 YL)METHYL]THIENO[3,2 D]PYRIMIDIN 2,4 DIONE; 1 (2' AMINO 2' CARBOXYETHYL) 3 [(2 CARBOXYTHIEN 3 YL)METHYL]THIENO[3,4 D]PYRIMIDIN 2,4 DIONE; 1 (2' AMINO 2' CARBOXYETHYL)THIENO[2,3 D]PYRIMIDIN 2,4 DIONE; 1 (2' AMINO 2' CARBOXYETHYL)THIENO[3,4 D]PYRIMIDIN 2,4 DIONE; 1 [2' AMINO 2' CARBOXYETHYL] 3 [(2 PHOSPHONOTHIEN 3 YL)METHYL]THIENO[3,2 D]PYRIMIDIN 2,4 DIONE; 1 [2' AMINO 2' CARBOXYETHYL] 3 [(2 PHOSPHONOTHIEN 3 YL)METHYL]THIENO[3,4 D]PYRIMIDIN 2,4 DIONE; KAINIC ACID RECEPTOR; KAINIC ACID RECEPTOR AGONIST; KAINIC ACID RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG;

EID: 79960174808     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2004078     Document Type: Article
Times cited : (19)

References (46)
  • 1
    • 0034065936 scopus 로고    scopus 로고
    • Glutamate as a neurotransmitter in the brain: Review of physiology and pathology
    • Meldrum, B. S. Glutamate as a neurotransmitter in the brain: review of physiology and pathology J. Nutr. 2000, 130, 1007S-1015S (Pubitemid 30173635)
    • (2000) Journal of Nutrition , vol.130 , Issue.4 SUPPL.
    • Meldrum, B.S.1
  • 2
    • 84882842721 scopus 로고    scopus 로고
    • Kainate receptor functions
    • In; Elsevier Ltd.: New York.
    • Lerma, J. Kainate receptor functions. In Encyclopedia of Neuroscience; Elsevier Ltd.: New York, 2009.
    • (2009) Encyclopedia of Neuroscience
    • Lerma, J.1
  • 4
    • 72049124287 scopus 로고    scopus 로고
    • X-ray structure, symmetry and mechanism of an AMPA-subtype glutamate receptor
    • Sobolevsky, A. I.; Rosconi, M. P.; Gouaux, E. X-ray structure, symmetry and mechanism of an AMPA-subtype glutamate receptor Nature 2009, 462, 745-756
    • (2009) Nature , vol.462 , pp. 745-756
    • Sobolevsky, A.I.1    Rosconi, M.P.2    Gouaux, E.3
  • 5
    • 0141540782 scopus 로고    scopus 로고
    • Kainate receptors and synaptic transmission
    • DOI 10.1016/S0301-0082(03)00122-9
    • Huettner, J. E. Kainate receptors and synaptic transmission Prog. Neurobiol. 2003, 70, 387-407 (Pubitemid 37159280)
    • (2003) Progress in Neurobiology , vol.70 , Issue.5 , pp. 387-407
    • Huettner, J.E.1
  • 6
    • 58049096661 scopus 로고    scopus 로고
    • Kainate receptors: Pharmacology, function and therapeutic potential
    • Jane, D. E.; Lodge, D.; Collingridge, G. L. Kainate receptors: pharmacology, function and therapeutic potential Neuropharmacology 2009, 56, 90-113
    • (2009) Neuropharmacology , vol.56 , pp. 90-113
    • Jane, D.E.1    Lodge, D.2    Collingridge, G.L.3
  • 7
    • 30844458571 scopus 로고    scopus 로고
    • Kainate receptor physiology
    • DOI 10.1016/j.coph.2005.08.004, PII S1471489205001797
    • Lerma, J. Kainate receptor physiology Curr. Opin. Pharmacol. 2006, 6, 89-97 (Pubitemid 43103824)
    • (2006) Current Opinion in Pharmacology , vol.6 , Issue.1 SPEC. ISS. , pp. 89-97
    • Lerma, J.1
  • 8
    • 0032712791 scopus 로고    scopus 로고
    • Kainate receptor pharmacology and physiology
    • Bleakman, D. Kainate receptor pharmacology and physiology Cell. Mol. Life Sci. 1999, 56, 558-566
    • (1999) Cell. Mol. Life Sci. , vol.56 , pp. 558-566
    • Bleakman, D.1
  • 11
    • 79951828235 scopus 로고    scopus 로고
    • Medicinal Chemistry of Competitive Kainate Receptor Antagonists
    • Larsen, A. M.; Bunch, L. Medicinal Chemistry of Competitive Kainate Receptor Antagonists ACS Chem. Neurosci. 2010, 2, 60-74
    • (2010) ACS Chem. Neurosci. , vol.2 , pp. 60-74
    • Larsen, A.M.1    Bunch, L.2
  • 12
    • 0030693165 scopus 로고    scopus 로고
    • Synthesis of Willardiine and 6-azawillardiine analogs: Pharmacological characterization on cloned homomeric human AMPA and kainate receptor subtypes
    • DOI 10.1021/jm9702387
    • Jane, D. E.; Hoo, K.; Kamboj, R.; Deverill, M.; Bleakman, D.; Mandelzys, A. Synthesis of willardiine and 6-azawillardiine analogs: pharmacological characterization on cloned homomeric human AMPA and kainate receptor subtypes J. Med. Chem. 1997, 40, 3645-3650 (Pubitemid 27465096)
    • (1997) Journal of Medicinal Chemistry , vol.40 , Issue.22 , pp. 3645-3650
    • Jane, D.E.1    Hoo, K.2    Kamboj, R.3    Deverill, M.4    Bleakman, D.5    Mandelzys, A.6
  • 14
    • 33646134848 scopus 로고    scopus 로고
    • Structure-activity relationship studies on N3-substituted willardiine derivatives acting as AMPA or kainate receptor antagonists
    • Dolman, N. P.; More, J. C.; Alt, A.; Knauss, J. L.; Troop, H. M.; Bleakman, D.; Collingridge, G. L.; Jane, D. E. Structure-activity relationship studies on N3-substituted willardiine derivatives acting as AMPA or kainate receptor antagonists J. Med. Chem. 2006, 49, 2579-2592
    • (2006) J. Med. Chem. , vol.49 , pp. 2579-2592
    • Dolman, N.P.1    More, J.C.2    Alt, A.3    Knauss, J.L.4    Troop, H.M.5    Bleakman, D.6    Collingridge, G.L.7    Jane, D.E.8
  • 19
    • 0028213957 scopus 로고
    • Synthesis of n-1-β-d-arabinofuranosyl and n-1-2'-deoxy-β-d- erythro- pentofuranosyl thieno[3,2-d] pyrimidine nucleosides
    • Fossey, H. L.; Laduree, D.; Robba, M. Synthesis of N -1-β- d -arabinosyl and N -1-2′-deoxy-β- d-erythro -pentofuranosyl thieno[3,2- d ]pyrimidine nucleosides Nucleosides Nucleotides 1994, 4, 925-937 (Pubitemid 24149958)
    • (1994) Nucleosides and Nucleotides , vol.13 , Issue.4 , pp. 925-937
    • Fossey, C.1    Landelle, H.2    Laduree, D.3    Robba, M.4
  • 20
    • 0029916027 scopus 로고    scopus 로고
    • Synthesis of chiral 1-(2'-amino-2'-carboxyethyl)-1,4-dihydro-6,7- quinoxaline-2,3-diones: α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionate receptor agonists and antagonists
    • DOI 10.1021/jm950632+
    • Sun, G.; Uretsky, N. J.; Wallace, L. J.; Shams, G.; Weinstein, D. M.; Miller, D. D. Synthesis of chiral 1-(2′-amino-2′-carboxyethyl)-1,4- dihydro-6,7-quinoxaline-2,3-diones: alpha-amino-3-hydroxy-5-methyl-4- isoxazolepropionate receptor agonists and antagonists J. Med. Chem. 1996, 39, 4430-4438 (Pubitemid 26359399)
    • (1996) Journal of Medicinal Chemistry , vol.39 , Issue.22 , pp. 4430-4438
    • Sun, G.1    Uretsky, N.J.2    Wallace, L.J.3    Shams, G.4    Weinstein, D.M.5    Miller, D.D.6
  • 21
    • 84983960649 scopus 로고
    • Reaktion von arylhalogeniden mit trialkylphosphiten und benzolphosphonigsäure-dialkylestern zu aromatischen phosphonsä ureestern und phosphinsäureestern unter nickelsalzkatalyse
    • Tavs, P. Reaktion von arylhalogeniden mit trialkylphosphiten und benzolphosphonigsäure-dialkylestern zu aromatischen phosphonsä ureestern und phosphinsäureestern unter nickelsalzkatalyse Chem. Ber. 1970, 103, 2428-2436
    • (1970) Chem. Ber. , vol.103 , pp. 2428-2436
    • Tavs, P.1
  • 22
    • 0032723799 scopus 로고    scopus 로고
    • An organomethallic route to zinc phosphonates and their intercalates
    • Gerbier, P.; Guerin, C.; Henner, B.; Unal, J. R. An organomethallic route to zinc phosphonates and their intercalates J. Mater. Chem. 1999, 9, 2559-2565
    • (1999) J. Mater. Chem. , vol.9 , pp. 2559-2565
    • Gerbier, P.1    Guerin, C.2    Henner, B.3    Unal, J.R.4
  • 23
    • 0009511858 scopus 로고
    • The reaction of dialkyl chlorophosphates with arylmagnesium halides
    • Bunger, A.; Dawson, N. D. The reaction of dialkyl chlorophosphates with arylmagnesium halides J. Org. Chem. 1951, 16, 1250-1254
    • (1951) J. Org. Chem. , vol.16 , pp. 1250-1254
    • Bunger, A.1    Dawson, N.D.2
  • 24
    • 78649940887 scopus 로고    scopus 로고
    • Mapping the ligand binding sites of kainate receptors: Molecular determinants of subunit-selective binding of the antagonist [3H]UBP310
    • Atlason, P. T.; Scholefield, C. L.; Eaves, R. J.; Mayo-Martin, M. B.; Jane, D. E.; Molnar, E. Mapping the ligand binding sites of kainate receptors: molecular determinants of subunit-selective binding of the antagonist [3H]UBP310 Mol. Pharmacol. 2010, 78, 1036-1045
    • (2010) Mol. Pharmacol. , vol.78 , pp. 1036-1045
    • Atlason, P.T.1    Scholefield, C.L.2    Eaves, R.J.3    Mayo-Martin, M.B.4    Jane, D.E.5    Molnar, E.6
  • 25
    • 78149496202 scopus 로고    scopus 로고
    • Binding site and ligand flexibility revealed by high resolution crystal structures of GluK1 competitive antagonists
    • Alushin, G. M.; Jane, D.; Mayer, M. L. Binding site and ligand flexibility revealed by high resolution crystal structures of GluK1 competitive antagonists Neuropharmacology 2010, 60, 126-134
    • (2010) Neuropharmacology , vol.60 , pp. 126-134
    • Alushin, G.M.1    Jane, D.2    Mayer, M.L.3
  • 26
    • 79960163766 scopus 로고    scopus 로고
    • Chemical Computing Group Inc.: Montreal.
    • MOE Software, 2006.08; Chemical Computing Group Inc.: Montreal, 2006.
    • (2006) MOE Software, 2006.08
  • 27
    • 33644999815 scopus 로고    scopus 로고
    • Crystal structures of the kainate receptor GluR5 ligand binding core dimer with novel GluR5-selective antagonists
    • Mayer, M. L.; Ghosal, A.; Dolman, N. P.; Jane, D. E. Crystal structures of the kainate receptor GluR5 ligand binding core dimer with novel GluR5-selective antagonists J. Neurosci. 2006, 26, 2852-2861
    • (2006) J. Neurosci. , vol.26 , pp. 2852-2861
    • Mayer, M.L.1    Ghosal, A.2    Dolman, N.P.3    Jane, D.E.4
  • 28
    • 13844266202 scopus 로고    scopus 로고
    • Crystal structures of the GluR5 and GluR6 ligand binding cores: Molecular mechanisms underlying kainate receptor selectivity
    • DOI 10.1016/j.neuron.2005.01.031
    • Mayer, M. L. Crystal structures of the GluR5 and GluR6 ligand binding cores: molecular mechanisms underlying kainate receptor selectivity Neuron 2005, 45, 539-552 (Pubitemid 40249866)
    • (2005) Neuron , vol.45 , Issue.4 , pp. 539-552
    • Mayer, M.L.1
  • 30
    • 58049104342 scopus 로고    scopus 로고
    • Antagonism of recombinant and native GluK3-containing kainate receptors
    • Perrais, D.; Pinheiro, P. S.; Jane, D. E.; Mulle, C. Antagonism of recombinant and native GluK3-containing kainate receptors Neuropharmacology 2009, 56, 131-140
    • (2009) Neuropharmacology , vol.56 , pp. 131-140
    • Perrais, D.1    Pinheiro, P.S.2    Jane, D.E.3    Mulle, C.4
  • 32
    • 0032216489 scopus 로고    scopus 로고
    • MacMolPlt: A graphical user interface for GAMESS
    • Bode, B. M.; Gordon, M. S. MacMolPlt: a graphical user interface for GAMESS J. Mol. Graphics Modell. 1998, 16 (133-138) 164
    • (1998) J. Mol. Graphics Modell. , vol.16 , Issue.133-138 , pp. 164
    • Bode, B.M.1    Gordon, M.S.2
  • 35
    • 33745209653 scopus 로고    scopus 로고
    • 3-Hydroxypyridazine 1-oxides as carboxylate bioisosteres: A new series of subtype-selective AMPA receptor agonists
    • Greenwood, J. R.; Mewett, K. N.; Allan, R. D.; Martin, B. O.; Pickering, D. S. 3-Hydroxypyridazine 1-oxides as carboxylate bioisosteres: a new series of subtype-selective AMPA receptor agonists Neuropharmacology 2006, 51, 52-59
    • (2006) Neuropharmacology , vol.51 , pp. 52-59
    • Greenwood, J.R.1    Mewett, K.N.2    Allan, R.D.3    Martin, B.O.4    Pickering, D.S.5
  • 36
    • 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 (Pubitemid 23113114)
    • (1993) Trends in Pharmacological Sciences , vol.14 , Issue.4 , pp. 110-112
    • Leff, P.1    Dougall, I.G.2
  • 37
    • 13844272397 scopus 로고    scopus 로고
    • Crystal structure of the kainate receptor GluR5 ligand-binding core in complex with (S)-glutamate
    • DOI 10.1016/j.febslet.2005.01.012
    • Naur, P.; Vestergaard, B.; Skov, L. K.; Egebjerg, J.; Gajhede, M.; Kastrup, J. S. Crystal structure of the kainate receptor GluR5 ligand-binding core in complex with (S)-glutamate FEBS Lett. 2005, 579, 1154-1160 (Pubitemid 40253550)
    • (2005) FEBS Letters , vol.579 , Issue.5 , pp. 1154-1160
    • Naur, P.1    Vestergaard, B.2    Skov, L.K.3    Egebjerg, J.4    Gajhede, M.5    Kastrup, J.S.6
  • 39
    • 0028103275 scopus 로고
    • The CCP4 suite: Programs for protein crystallography
    • 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
    • 0032964481 scopus 로고    scopus 로고
    • Automated protein model building combined with iterative structure refinement
    • DOI 10.1038/8263
    • Perrakis, A.; Morris, R.; Lamzin, V. S. Automated protein model building combined with iterative structure refinement Nature Struct. Biol. 1999, 6, 458-463 (Pubitemid 29218016)
    • (1999) Nature Structural Biology , vol.6 , Issue.5 , pp. 458-463
    • Perrakis, A.1    Morris, R.2    Lamzin, V.S.3
  • 45
    • 0036888353 scopus 로고    scopus 로고
    • Improvements in the analysis of domain motions in proteins from conformational change: DynDom version 1.50
    • DOI 10.1016/S1093-3263(02)00140-7, PII S1093326302001407
    • Hayward, S.; Lee, R. A. Improvements in the analysis of domain motions in proteins from conformational change: DynDom version 1.50 J. Mol. Graphics Modell. 2002, 21, 181-183 (Pubitemid 35279848)
    • (2002) Journal of Molecular Graphics and Modelling , vol.21 , Issue.3 , pp. 181-183
    • Hayward, S.1    Lee, R.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.