메뉴 건너뛰기




Volumn 53, Issue 15, 2010, Pages 5801-5812

Discovery of N -[(2 s)-5-(6-fluoro-3-pyridinyl)-2,3-dihydro-1 H -inden-2-yl]-2-propanesulfonamide, a novel clinical AMPA receptor positive modulator

Author keywords

[No Author keywords available]

Indexed keywords

AMPA RECEPTOR AGONIST; N [5 (6 FLUORO 3 PYRIDINYL) 2,3 DIHYDRO 1H INDEN 2 YL] 2 PROPANESULFONAMIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; AMPA RECEPTOR; INDENE DERIVATIVE; N (5 (6 FLUORO 3 PYRIDINYL) 2,3 DIHYDRO 1H INDEN 2 YL) 2 PROPANESULFONAMIDE; N-(5-(6-FLUORO-3-PYRIDINYL)-2,3-DIHYDRO-1H-INDEN-2-YL)-2-PROPANESULFONAMIDE; PLASMA PROTEIN; SULFONAMIDE;

EID: 77955368627     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1005429     Document Type: Article
Times cited : (41)

References (36)
  • 1
    • 42949123365 scopus 로고    scopus 로고
    • Targeting the glutamatergic system to develop novel, improved therapeutics for mood disorders
    • Sanacora, G.; Zarate, C. A.; Krystal, J. H.; Manji, H. K. Targeting the glutamatergic system to develop novel, improved therapeutics for mood disorders Nature Rev. Drug Discovery 2008, 7, 426-437
    • (2008) Nature Rev. Drug Discovery , vol.7 , pp. 426-437
    • Sanacora, G.1    Zarate, C.A.2    Krystal, J.H.3    Manji, H.K.4
  • 2
    • 42749091755 scopus 로고    scopus 로고
    • The role of AMPA receptor modulation in the treatment of neuropsychiatric diseases
    • Zarate, C. A., Jr.; Manji, H. K. The role of AMPA receptor modulation in the treatment of neuropsychiatric diseases Exp. Neurol. 2008, 211, 7-10
    • (2008) Exp. Neurol. , vol.211 , pp. 7-10
    • Zarate Jr., C.A.1    Manji, H.K.2
  • 3
    • 17844407467 scopus 로고    scopus 로고
    • Therapeutic potential of positive AMPA modulators and their relationship to AMPA receptor subunits. A review of preclinical data
    • Black, M. D. Therapeutic potential of positive AMPA modulators and their relationship to AMPA receptor subunits. A review of preclinical data Psychopharmacology (Berlin) 2005, 179, 154-163
    • (2005) Psychopharmacology (Berlin) , vol.179 , pp. 154-163
    • Black, M.D.1
  • 4
    • 0027143781 scopus 로고
    • A drug that facilitates glutamatergic transmission reduces exploratory activity and improves performance in a learning-dependent task
    • Granger, R.; Staubli, U.; Davis, M.; Perez, Y.; Nilsson, L.; Rogers, G. A.; Lynch, G. A drug that facilitates glutamatergic transmission reduces exploratory activity and improves performance in a learning-dependent task Synapse 1993, 15, 326-329
    • (1993) Synapse , vol.15 , pp. 326-329
    • Granger, R.1    Staubli, U.2    Davis, M.3    Perez, Y.4    Nilsson, L.5    Rogers, G.A.6    Lynch, G.7
  • 5
    • 33748762214 scopus 로고    scopus 로고
    • Ampakines and the threefold path to cognitive enhancement
    • Lynch, G.; Gall, C. M. Ampakines and the threefold path to cognitive enhancement Trends Neurosci. 2006, 29, 554-562
    • (2006) Trends Neurosci. , vol.29 , pp. 554-562
    • Lynch, G.1    Gall, C.M.2
  • 7
    • 0031912995 scopus 로고    scopus 로고
    • Glutamate receptors in the mammalian central nervous system
    • Ozawa, S.; Kamiya, H.; Tsuzuki, K. Glutamate receptors in the mammalian central nervous system Prog. Neurobiol. 1998, 54, 581-618
    • (1998) Prog. Neurobiol. , vol.54 , pp. 581-618
    • Ozawa, S.1    Kamiya, H.2    Tsuzuki, K.3
  • 8
    • 0035819074 scopus 로고    scopus 로고
    • Heteromeric AMPA receptors assemble with a preferred subunit stoichiometry and spatial arrangement
    • Mansour, M.; Nagarajan, N.; Nehring, R. B.; Clements, J. D.; Rosenmund, C. Heteromeric AMPA receptors assemble with a preferred subunit stoichiometry and spatial arrangement Neuron 2001, 32, 841-853
    • (2001) Neuron , vol.32 , pp. 841-853
    • Mansour, M.1    Nagarajan, N.2    Nehring, R.B.3    Clements, J.D.4    Rosenmund, C.5
  • 9
    • 7444240214 scopus 로고    scopus 로고
    • The Three-dimensional Structure of an Ionotropic Glutamate Receptor Reveals a Dimer-of-Dimers Assembly
    • Tichelaar, W.; Safferling, M.; Keinanen, K.; Stark, H.; Madden, D. R. The Three-dimensional Structure of an Ionotropic Glutamate Receptor Reveals a Dimer-of-Dimers Assembly J. Mol. Biol. 2004, 344, 435-442
    • (2004) J. Mol. Biol. , vol.344 , pp. 435-442
    • Tichelaar, W.1    Safferling, M.2    Keinanen, K.3    Stark, H.4    Madden, D.R.5
  • 10
    • 0033636314 scopus 로고    scopus 로고
    • Mechanisms for activation and antagonism of an AMPA-sensitive glutamate receptor: crystal structures of the GluR2 ligand binding core
    • Armstrong, N.; Gouaux, E. Mechanisms for activation and antagonism of an AMPA-sensitive glutamate receptor: crystal structures of the GluR2 ligand binding core Neuron 2000, 28, 165-181
    • (2000) Neuron , vol.28 , pp. 165-181
    • Armstrong, N.1    Gouaux, E.2
  • 11
    • 0442279279 scopus 로고    scopus 로고
    • Structure and function of AMPA receptors
    • Gouaux, E. Structure and function of AMPA receptors J. Physiol. 2004, 554, 249-253
    • (2004) J. Physiol. , vol.554 , pp. 249-253
    • Gouaux, E.1
  • 13
    • 45849133048 scopus 로고    scopus 로고
    • Regulation of AMPA receptor gating and pharmacology by TARP auxiliary subunits
    • Milstein, A. D.; Nicoll, R. A. Regulation of AMPA receptor gating and pharmacology by TARP auxiliary subunits Trends Pharmacol. Sci. 2008, 29, 333-339
    • (2008) Trends Pharmacol. Sci. , vol.29 , pp. 333-339
    • Milstein, A.D.1    Nicoll, R.A.2
  • 15
    • 34748849546 scopus 로고    scopus 로고
    • Stargazin attenuates intracellular polyamine block of calcium-permeable AMPA receptors
    • Soto, D.; Coombs, I. D.; Kelly, L.; Farrant, M.; Cull-Candy, S. G. Stargazin attenuates intracellular polyamine block of calcium-permeable AMPA receptors Nature Neurosci. 2007, 10, 1260-1267
    • (2007) Nature Neurosci. , vol.10 , pp. 1260-1267
    • Soto, D.1    Coombs, I.D.2    Kelly, L.3    Farrant, M.4    Cull-Candy, S.G.5
  • 16
    • 0029583151 scopus 로고
    • Molecular dissection of the agonist binding site of an AMPA receptor
    • Kuusinen, A.; Arvola, M.; Keinanen, K. Molecular dissection of the agonist binding site of an AMPA receptor EMBO J. 1995, 14, 6327-6332
    • (1995) EMBO J. , vol.14 , pp. 6327-6332
    • Kuusinen, A.1    Arvola, M.2    Keinanen, K.3
  • 17
    • 0032578635 scopus 로고    scopus 로고
    • Structure of a glutamate-receptor ligand-binding core in complex with kainate
    • Armstrong, N.; Sun, Y.; Chen, G. Q.; Gouaux, E. Structure of a glutamate-receptor ligand-binding core in complex with kainate Nature 1998, 395, 913-917
    • (1998) Nature , vol.395 , pp. 913-917
    • Armstrong, N.1    Sun, Y.2    Chen, G.Q.3    Gouaux, E.4
  • 18
    • 25644454403 scopus 로고    scopus 로고
    • Mechanism of positive allosteric modulators acting on AMPA receptors
    • Jin, R.; Clark, S.; Weeks, A. M.; Dudman, J. T.; Gouaux, E.; Partin, K. M. Mechanism of positive allosteric modulators acting on AMPA receptors J. Neurosci. 2005, 25, 9027-9036
    • (2005) J. Neurosci. , vol.25 , pp. 9027-9036
    • Jin, R.1    Clark, S.2    Weeks, A.M.3    Dudman, J.T.4    Gouaux, E.5    Partin, K.M.6
  • 19
    • 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
  • 21
    • 0038237099 scopus 로고    scopus 로고
    • Identification of a site in GluR1 and GluR2 that is important for modulation of deactivation and desensitization
    • Leever, J. D.; Clark, S.; Weeks, A. M.; Partin, K. M. Identification of a site in GluR1 and GluR2 that is important for modulation of deactivation and desensitization Mol. Pharmacol. 2003, 64, 5-10
    • (2003) Mol. Pharmacol. , vol.64 , pp. 5-10
    • Leever, J.D.1    Clark, S.2    Weeks, A.M.3    Partin, K.M.4
  • 22
    • 36749075049 scopus 로고    scopus 로고
    • Prediction of the binding mode of biarylpropylsulfonamide allosteric AMPA receptor modulators based on docking, GRID molecular interaction fields and 3D-QSAR analysis
    • Harpsoe, K.; Liljefors, T.; Balle, T. Prediction of the binding mode of biarylpropylsulfonamide allosteric AMPA receptor modulators based on docking, GRID molecular interaction fields and 3D-QSAR analysis J. Mol. Graphics Modell. 2008, 26, 874-883
    • (2008) J. Mol. Graphics Modell. , vol.26 , pp. 874-883
    • Harpsoe, K.1    Liljefors, T.2    Balle, T.3
  • 23
    • 33748612166 scopus 로고    scopus 로고
    • Recent advances in positive allosteric modulators of the AMPA receptor
    • Morrow, J. A.; Maclean, J. K.; Jamieson, C. Recent advances in positive allosteric modulators of the AMPA receptor Curr. Opin. Drug Discovery Dev. 2006, 9, 571-579
    • (2006) Curr. Opin. Drug Discovery Dev. , vol.9 , pp. 571-579
    • Morrow, J.A.1    Maclean, J.K.2    Jamieson, C.3
  • 25
    • 77951694715 scopus 로고    scopus 로고
    • Challenges for and current status of research into positive modulators of AMPA receptors
    • Ward, S. E.; Bax, B. D.; Harries, M. Challenges for and current status of research into positive modulators of AMPA receptors Br. J. Pharmacol. 2010, 160, 181-190
    • (2010) Br. J. Pharmacol. , vol.160 , pp. 181-190
    • Ward, S.E.1    Bax, B.D.2    Harries, M.3
  • 26
    • 1542503699 scopus 로고    scopus 로고
    • Computational models to predict blood?brain barrier permeation and CNS activity
    • Subramanian, G.; Kitchen, D. B. Computational models to predict blood?brain barrier permeation and CNS activity J. Comput-Aided Mol. Des. 2003, 17, 643-664
    • (2003) J. Comput-Aided Mol. Des. , vol.17 , pp. 643-664
    • Subramanian, G.1    Kitchen, D.B.2
  • 27
    • 0000825620 scopus 로고    scopus 로고
    • Efficient and practical syntheses of (R)-(5-amino-2,3-dihydro-1 H -inden-2-yl)carbamic acid methyl ester
    • Prashad, M.; Hu, B.; Har, D.; Repic, O.; Blacklock, T. J.; Acemoglu, M. Efficient and practical syntheses of (R)-(5-amino-2,3-dihydro-1 H -inden-2-yl)carbamic acid methyl ester Adv. Synth. Catal. 2001, 343, 461-472
    • (2001) Adv. Synth. Catal. , vol.343 , pp. 461-472
    • Prashad, M.1    Hu, B.2    Har, D.3    Repic, O.4    Blacklock, T.J.5    Acemoglu, M.6
  • 28
    • 0023691166 scopus 로고
    • A new one-trial test for neurobiological studies of memory in rats. 1: Behavioral data
    • Ennaceur, A.; Delacour, J. A new one-trial test for neurobiological studies of memory in rats. 1: Behavioral data Behav. Brain Res. 1988, 31, 47-59
    • (1988) Behav. Brain Res. , vol.31 , pp. 47-59
    • Ennaceur, A.1    Delacour, J.2
  • 29
    • 0346057791 scopus 로고    scopus 로고
    • The 5-HT(6) receptor antagonist SB-271046 reverses scopolamine-disrupted consolidation of a passive avoidance task and ameliorates spatial task deficits in aged rats
    • Foley, A. G.; Murphy, K. J.; Hirst, W. D.; Gallagher, H. C.; Hagan, J. J.; Upton, N.; Walsh, F. S.; Regan, C. M. The 5-HT(6) receptor antagonist SB-271046 reverses scopolamine-disrupted consolidation of a passive avoidance task and ameliorates spatial task deficits in aged rats Neuropsychopharmacology 2004, 29, 93-100
    • (2004) Neuropsychopharmacology , vol.29 , pp. 93-100
    • Foley, A.G.1    Murphy, K.J.2    Hirst, W.D.3    Gallagher, H.C.4    Hagan, J.J.5    Upton, N.6    Walsh, F.S.7    Regan, C.M.8
  • 30
    • 68349086837 scopus 로고    scopus 로고
    • Distinct structural features of cyclothiazide are responsible for effects on peak current amplitude and desensitization kinetics at iGluR2
    • Hald, H.; Ahring, P. K.; Timmermann, D. B.; Liljefors, T.; Gajhede, M.; Kastrup, J. S. Distinct structural features of cyclothiazide are responsible for effects on peak current amplitude and desensitization kinetics at iGluR2 J. Mol. Biol. 2009, 391, 906-917
    • (2009) J. Mol. Biol. , vol.391 , pp. 906-917
    • Hald, H.1    Ahring, P.K.2    Timmermann, D.B.3    Liljefors, T.4    Gajhede, M.5    Kastrup, J.S.6
  • 31
    • 0037066903 scopus 로고    scopus 로고
    • Pharmacological properties of rat alpha 7 nicotinic receptors expressed in native and recombinant cell systems
    • Virginio, C.; Giacometti, A.; Aldegheri, L.; Rimland, J. M.; Terstappen, G. C. Pharmacological properties of rat alpha 7 nicotinic receptors expressed in native and recombinant cell systems Eur. J. Pharmacol. 2002, 445, 153-161
    • (2002) Eur. J. Pharmacol. , vol.445 , pp. 153-161
    • Virginio, C.1    Giacometti, A.2    Aldegheri, L.3    Rimland, J.M.4    Terstappen, G.C.5
  • 32
    • 33646588654 scopus 로고    scopus 로고
    • Pharmacological insights obtained from structure?function studies of ionotropic glutamate receptors
    • Chen, P. E.; Wyllie, D. J. Pharmacological insights obtained from structure?function studies of ionotropic glutamate receptors Br. J. Pharmacol. 2006, 147, 839-853
    • (2006) Br. J. Pharmacol. , vol.147 , pp. 839-853
    • Chen, P.E.1    Wyllie, D.J.2
  • 33
    • 1842412059 scopus 로고
    • Data collection and processing
    • Ed.; SERC Daresbury Laboratory: Warrington, UK:
    • Otwinowski, Z. Data collection and processing. In Proceedings of CCP4 Study Weekend; Sawyer, L., Ed.; SERC Daresbury Laboratory: Warrington, UK: 1993; pp 56 - 62.
    • (1993) Proceedings of CCP4 Study Weekend , pp. 56-62
    • Otwinowski, Z.1    Sawyer, L.2
  • 35
    • 84889120137 scopus 로고
    • Improved methods for building protein models in electron density maps and the location of errors in these models
    • Jones, T. A.; Zou, J. Y.; Cowan, S. W.; Kjeldgaard, M. Improved methods for building protein models in electron density maps and the location of errors in these models Acta Crystallogr., Sect. A: Found. Crystallogr. 1991, 47, 110-119
    • (1991) Acta Crystallogr., Sect. A: Found. Crystallogr. , vol.47 , pp. 110-119
    • Jones, T.A.1    Zou, J.Y.2    Cowan, S.W.3    Kjeldgaard, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.