메뉴 건너뛰기




Volumn 55, Issue 5, 2012, Pages 2388-2405

Discovery of 1,4-disubstituted 3-cyano-2-pyridones: A new class of positive allosteric modulators of the metabotropic glutamate 2 receptor

Author keywords

[No Author keywords available]

Indexed keywords

1 BUTYL 4 [3 FLUORO 4 (2 METHYLPYRIDIN 4 YLOXY)PHENYL] 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBONITRILE; 4 AMINO 2 THIABICYCLO[3.1.0]HEXANE 4,6 DICARBOXYLIC ACID 2,2 DIOXIDE; CYANIDE; GLUTAMATE RECEPTOR 2; POMAGLUMETAD METHIONIL; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84858052780     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2016864     Document Type: Article
Times cited : (32)

References (54)
  • 1
    • 0033851295 scopus 로고    scopus 로고
    • L -Glutamate as a central neurotransmitter: Looking back
    • Watkins, J. C. l -Glutamate as a central neurotransmitter: looking back Biochem. Soc. Trans. 2000, 28, 297-310
    • (2000) Biochem. Soc. Trans. , vol.28 , pp. 297-310
    • Watkins, J.C.1
  • 2
    • 0030995878 scopus 로고    scopus 로고
    • Pharmacology and functions of metabotropic glutamate receptors
    • Conn, P. J.; Pin, J. P. Pharmacology and functions of metabotropic glutamate receptors Annu. Rev. Pharmacol. Toxicol. 1997, 37, 205-237
    • (1997) Annu. Rev. Pharmacol. Toxicol. , vol.37 , pp. 205-237
    • Conn, P.J.1    Pin, J.P.2
  • 3
    • 17744387125 scopus 로고    scopus 로고
    • Ionotropic and metabotropic glutamate receptor structure and pharmacology
    • Kew, J. N. C.; Kemp, J. A. Ionotropic and metabotropic glutamate receptor structure and pharmacology Psyhopharmacology 2005, 179, 4-29
    • (2005) Psyhopharmacology , vol.179 , pp. 4-29
    • Kew, J.N.C.1    Kemp, J.A.2
  • 4
    • 0038662595 scopus 로고    scopus 로고
    • Evolution, structure, and activation mechanism of family 3/C G-protein-coupled receptors
    • Pin, J. P.; Galvez, T.; Prezeau, L. Evolution, structure, and activation mechanism of family 3/C G-protein-coupled receptors Pharmacol. Ther. 2003, 98, 325-354
    • (2003) Pharmacol. Ther. , vol.98 , pp. 325-354
    • Pin, J.P.1    Galvez, T.2    Prezeau, L.3
  • 5
    • 33845973375 scopus 로고    scopus 로고
    • Structure, pharmacology and therapeutic prospects of family C G-protein coupled receptors
    • Brauner-Osborne, H.; Wellendorph, P.; Jensen, A. A. Structure, pharmacology and therapeutic prospects of family C G-protein coupled receptors Curr. Drug Targets 2007, 8, 169-184
    • (2007) Curr. Drug Targets , vol.8 , pp. 169-184
    • Brauner-Osborne, H.1    Wellendorph, P.2    Jensen, A.A.3
  • 7
    • 0033844601 scopus 로고    scopus 로고
    • Regulation of neurotransmitter release by metabotropic glutamate receptors
    • Cartmell, J.; Schoepp, D. D. Regulation of neurotransmitter release by metabotropic glutamate receptors J. Neurochem. 2000, 75, 889-907
    • (2000) J. Neurochem. , vol.75 , pp. 889-907
    • Cartmell, J.1    Schoepp, D.D.2
  • 8
    • 0027190384 scopus 로고
    • Distribution of the messenger RNA for metabotropic glutamate receptor, mGlu2, in the central nervous system of the rat
    • Ohishi, H.; Shigemoto, R.; Nakanishi, S.; Mizuno, N. Distribution of the messenger RNA for metabotropic glutamate receptor, mGlu2, in the central nervous system of the rat Neuroscience 1993, 53, 1009-1018
    • (1993) Neuroscience , vol.53 , pp. 1009-1018
    • Ohishi, H.1    Shigemoto, R.2    Nakanishi, S.3    Mizuno, N.4
  • 10
    • 39149083048 scopus 로고    scopus 로고
    • Distribution of metabotropic glutamate 2 and 3 receptors in the rat forebrain: Implication in emotional responses and central disinhibition
    • Gu, G.; Lorrain, D. S.; Wei, H.; Cole, R. L.; Zhang, X.; Daggett, L. P.; Schaffhauser, H. J.; Bristow, L. J.; Lechner, S. M. Distribution of metabotropic glutamate 2 and 3 receptors in the rat forebrain: implication in emotional responses and central disinhibition Brain Res. 2008, 1197, 47-62
    • (2008) Brain Res. , vol.1197 , pp. 47-62
    • Gu, G.1    Lorrain, D.S.2    Wei, H.3    Cole, R.L.4    Zhang, X.5    Daggett, L.P.6    Schaffhauser, H.J.7    Bristow, L.J.8    Lechner, S.M.9
  • 11
    • 67649981850 scopus 로고    scopus 로고
    • Differential expression of metabotropic glutamate receptors 2 and 3 in schizophrenia: A mechanism for antipsychotic drug action?
    • Ghose, S.; Gleason, K. A.; Potts, B. W.; Lewis-Amezcua, K.; Tamminga, C. A. Differential expression of metabotropic glutamate receptors 2 and 3 in schizophrenia: a mechanism for antipsychotic drug action? Am. J. Psychiatry 2009, 166, 812-820
    • (2009) Am. J. Psychiatry , vol.166 , pp. 812-820
    • Ghose, S.1    Gleason, K.A.2    Potts, B.W.3    Lewis-Amezcua, K.4    Tamminga, C.A.5
  • 13
    • 0011900802 scopus 로고    scopus 로고
    • Preclinical pharmacology of mGluR2/3 receptor agonists: Novel agents for schizophrenia?
    • Schoepp, D. D.; Marek, G. J. Preclinical pharmacology of mGluR2/3 receptor agonists: novel agents for schizophrenia? CNS Neurol. Disord.: Drug Targets 2002, 1, 215-225
    • (2002) CNS Neurol. Disord.: Drug Targets , vol.1 , pp. 215-225
    • Schoepp, D.D.1    Marek, G.J.2
  • 14
    • 58149119377 scopus 로고    scopus 로고
    • Activation of metabotropic glutamate receptors as a novel approach for the treatment of schizophrenia
    • Conn, P. J.; Lindsley, C. W.; Jones, C. K. Activation of metabotropic glutamate receptors as a novel approach for the treatment of schizophrenia Trends Pharmacol. Sci. 2009, 30, 25-30
    • (2009) Trends Pharmacol. Sci. , vol.30 , pp. 25-30
    • Conn, P.J.1    Lindsley, C.W.2    Jones, C.K.3
  • 15
    • 79953311403 scopus 로고    scopus 로고
    • Targeting of metabotropic glutamate receptors for the treatment of schizophrenia
    • Shigeyuki, C.; Hirohiko, H. Targeting of metabotropic glutamate receptors for the treatment of schizophrenia Curr. Pharm. Des. 2011, 17, 94-102
    • (2011) Curr. Pharm. Des. , vol.17 , pp. 94-102
    • Shigeyuki, C.1    Hirohiko, H.2
  • 18
    • 77954571475 scopus 로고    scopus 로고
    • Recent developments in metabotropic glutamate receptors as novel drug targets
    • O'Neill, M. J.; Fell, M. J.; Svensson, K. A.; Witkin, J. M.; Mitchell, S. N. Recent developments in metabotropic glutamate receptors as novel drug targets Drugs Future 2010, 35, 307-324
    • (2010) Drugs Future , vol.35 , pp. 307-324
    • O'Neill, M.J.1    Fell, M.J.2    Svensson, K.A.3    Witkin, J.M.4    Mitchell, S.N.5
  • 19
    • 80051770211 scopus 로고    scopus 로고
    • Recent progress in the synthesis and characterization of group II metabotropic glutamate receptor allosteric modulators
    • Sheffler, D. J.; Pinkerton, A. B.; Dahl, R.; Markou, A.; Cosford, N. D. P. Recent progress in the synthesis and characterization of group II metabotropic glutamate receptor allosteric modulators ACS Chem. Neurosci. 2011, 2, 342-353
    • (2011) ACS Chem. Neurosci. , vol.2 , pp. 342-353
    • Sheffler, D.J.1    Pinkerton, A.B.2    Dahl, R.3    Markou, A.4    Cosford, N.D.P.5
  • 20
    • 38949207272 scopus 로고    scopus 로고
    • The mGlu2 but not the mGlu3 receptor mediates the actions of the mGluR2/3 agonist, LY379268, in mouse models predictive of antipsychotic activity
    • Wooley, M. L.; Pemberton, D. J.; Bate, S.; Corti, C.; Jones, D. M. The mGlu2 but not the mGlu3 receptor mediates the actions of the mGluR2/3 agonist, LY379268, in mouse models predictive of antipsychotic activity Psychopharmacology 2008, 196, 431-440
    • (2008) Psychopharmacology , vol.196 , pp. 431-440
    • Wooley, M.L.1    Pemberton, D.J.2    Bate, S.3    Corti, C.4    Jones, D.M.5
  • 21
    • 45749139623 scopus 로고    scopus 로고
    • Evidence for the role of metabotropic glutamate (mGlu)2 not mGlu3 receptors in the preclinical antipsychotic pharmacology of the mGlu2/3 receptor agonist (-)-(1 R,4 S,5 S,6 S)-4-amino-2-sulfonylbicyclo[3.1.0]hexane-4,6- dicarboxylic acid (LY404039)
    • Fell, M. J.; Svensson, K. A.; Johnson, B. G.; Schoepp, D. D. Evidence for the role of metabotropic glutamate (mGlu)2 not mGlu3 receptors in the preclinical antipsychotic pharmacology of the mGlu2/3 receptor agonist (-)-(1 R,4 S,5 S,6 S)-4-amino-2-sulfonylbicyclo[3.1.0]hexane-4,6-dicarboxylic acid (LY404039) J. Pharmacol. Exp. Ther. 2008, 326, 209-217
    • (2008) J. Pharmacol. Exp. Ther. , vol.326 , pp. 209-217
    • Fell, M.J.1    Svensson, K.A.2    Johnson, B.G.3    Schoepp, D.D.4
  • 22
    • 0034757740 scopus 로고    scopus 로고
    • B receptors open new routes for the development of drugs targeting family 3 G-protein-coupled receptors
    • B receptors open new routes for the development of drugs targeting family 3 G-protein-coupled receptors Mol. Pharmacol. 2001, 60, 881-884
    • (2001) Mol. Pharmacol. , vol.60 , pp. 881-884
    • Pin, J.P.1    Parmentier, M.-L.2    Prezeau, L.3
  • 24
    • 78751545477 scopus 로고    scopus 로고
    • Progress in the development of positive allosteric modulators of the metabotropic glutamate receptor 2
    • Trabanco, A. A.; Cid, J. M.; Lavreysen, H.; Macdonald, G. J.; Tresadern, G. Progress in the development of positive allosteric modulators of the metabotropic glutamate receptor 2 Curr. Med. Chem. 2011, 18, 47-68
    • (2011) Curr. Med. Chem. , vol.18 , pp. 47-68
    • Trabanco, A.A.1    Cid, J.M.2    Lavreysen, H.3    MacDonald, G.J.4    Tresadern, G.5
  • 26
    • 0038155299 scopus 로고    scopus 로고
    • Discovery of allosteric potentiators for the metabotropic glutamate 2 receptor: Synthesis and subtype selectivity of N -(4-(2-methoxyphenoxy)phenyl)- N -(2,2,2-trifluoroethylsulfonyl)pyrid-3-ylmethylamine
    • Johnson, M. P.; Baez, M.; Jagdmann, G. E.; Britton, T. C.; Large, T. H.; Callagaro, D. O.; Tizzano, J. P.; Monn, J. A.; Schoepp, D. D. Discovery of allosteric potentiators for the metabotropic glutamate 2 receptor: synthesis and subtype selectivity of N -(4-(2-methoxyphenoxy)phenyl)- N -(2,2,2- trifluoroethylsulfonyl)pyrid-3-ylmethylamine J. Med. Chem. 2003, 46, 3189-3192
    • (2003) J. Med. Chem. , vol.46 , pp. 3189-3192
    • Johnson, M.P.1    Baez, M.2    Jagdmann, G.E.3    Britton, T.C.4    Large, T.H.5    Callagaro, D.O.6    Tizzano, J.P.7    Monn, J.A.8    Schoepp, D.D.9
  • 27
    • 2442432348 scopus 로고    scopus 로고
    • SAR study of a subtype selective allosteric potentiator of metabotropic glutamate 2 receptor, N -(4-phenoxyphenyl)- N -(3-pyridylmethyl) ethanesulfonamide
    • Barda, D. A.; Wang, Z.-Q.; Britton, T. C.; Henry, S. S.; Jagdmann, G. E.; Coleman, D. S.; Johnson, M. P.; Andis, S. L.; Schoepp, D. D. SAR study of a subtype selective allosteric potentiator of metabotropic glutamate 2 receptor, N -(4-phenoxyphenyl)- N -(3-pyridylmethyl)ethanesulfonamide Bioorg. Med. Chem. Lett. 2004, 14, 3099-3102
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 3099-3102
    • Barda, D.A.1    Wang, Z.-Q.2    Britton, T.C.3    Henry, S.S.4    Jagdmann, G.E.5    Coleman, D.S.6    Johnson, M.P.7    Andis, S.L.8    Schoepp, D.D.9
  • 29
    • 5344253953 scopus 로고    scopus 로고
    • Allosteric potentiators of the metabotropic glutamate receptor 2 (mGlu2). Part 1: Identification and synthesis of phenyl-tetrazolyl acetophenones
    • Pinkerton, A. B.; Cube, R. V.; Hutchinson, J. H.; Rowe, B. A.; Schaffhauser, H.; Zhao, X.; Daggett, L. P.; Vernier, J.-M. Allosteric potentiators of the metabotropic glutamate receptor 2 (mGlu2). Part 1: identification and synthesis of phenyl-tetrazolyl acetophenones Bioorg. Med. Chem. Lett. 2004, 14, 5329-5332
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 5329-5332
    • Pinkerton, A.B.1    Cube, R.V.2    Hutchinson, J.H.3    Rowe, B.A.4    Schaffhauser, H.5    Zhao, X.6    Daggett, L.P.7    Vernier, J.-M.8
  • 30
    • 7044235517 scopus 로고    scopus 로고
    • Allosteric potentiators of the metabotropic glutamate receptor 2 (mGlu2). Part 2: 4-thiopyridyl acetophenones as non-tetrazole containing mGlu2 receptor potentiators
    • Pinkerton, A. B.; Cube, R. V.; Hutchinson, J. H.; James, J. K.; Gardner, M. F.; Schaffhauser, H.; Rowe, B. A.; Daggett, L. P.; Vernier, J.-M. Allosteric potentiators of the metabotropic glutamate receptor 2 (mGlu2). Part 2: 4-thiopyridyl acetophenones as non-tetrazole containing mGlu2 receptor potentiators Bioorg. Med. Chem. Lett. 2004, 14, 5867-5872
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 5867-5872
    • Pinkerton, A.B.1    Cube, R.V.2    Hutchinson, J.H.3    James, J.K.4    Gardner, M.F.5    Schaffhauser, H.6    Rowe, B.A.7    Daggett, L.P.8    Vernier, J.-M.9
  • 31
    • 17144417749 scopus 로고    scopus 로고
    • 3-(2-Ethoxy-4-{4-[3-hydroxy-2-methyl-4-(3-methylbutanoyl)-phenoxy]butoxy} phenylpropanoic acid: A brain penetrant allosteric potentiator at the metabotropic glutamate receptor 2 (mGluR2)
    • Cube, R. V.; Vernier, J.-M.; Hutchinson, J. H.; Gardner, M. F.; James, J. K.; Rowe, B. A.; Schaffhauser, H.; Daggett, L.; Pinkerton, A. B. 3-(2-Ethoxy-4-{4-[3-hydroxy-2-methyl-4-(3-methylbutanoyl)-phenoxy]butoxy} phenylpropanoic acid: a brain penetrant allosteric potentiator at the metabotropic glutamate receptor 2 (mGluR2) Bioorg. Med. Chem. Lett. 2005, 15, 2389-2393
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 2389-2393
    • Cube, R.V.1    Vernier, J.-M.2    Hutchinson, J.H.3    Gardner, M.F.4    James, J.K.5    Rowe, B.A.6    Schaffhauser, H.7    Daggett, L.8    Pinkerton, A.B.9
  • 48
    • 84858010167 scopus 로고    scopus 로고
    • Unpublished results.
    • Unpublished results.
  • 53
    • 0031570357 scopus 로고    scopus 로고
    • Microtiter plate assays for inhibition of human, drug-metabolizing cytochromes P450
    • Crespi, C. L.; Miller, V. P.; Penman, B. W. Microtiter plate assays for inhibition of human, drug-metabolizing cytochromes P450 Anal. Biochem. 1997, 248, 188-190
    • (1997) Anal. Biochem. , vol.248 , pp. 188-190
    • Crespi, C.L.1    Miller, V.P.2    Penman, B.W.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.