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Volumn 47, Issue 9, 2004, Pages 2348-2355

Dopamine D4 Ligands and Models of Receptor Activation: 2-(4-Pyridin-2-ylpiperazin-1-ymethyl)-1H-benzimidazole and Related Heteroarylmethylarylpiperazines Exhibit a Substituent Effect Responsible for Additional Efficacy Tuning

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 PYRIDIN 2 YLPIPERAZIN 1 YLMETHYL) 1H BENZIMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; DOPAMINE 4 RECEPTOR; G PROTEIN COUPLED RECEPTOR; PHENYLPIPERAZINE; PIPERAZINE DERIVATIVE; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG; DOPAMINE 2 RECEPTOR; DRD4 PROTEIN, HUMAN; LIGAND; PYRIDINE DERIVATIVE;

EID: 1842628624     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0305669     Document Type: Article
Times cited : (38)

References (62)
  • 1
    • 0032581639 scopus 로고    scopus 로고
    • G-Protein Coupled Receptors: Models, Mutagenesis, and Drug Design
    • Bikker, J. A.; Trumpp-Kallmeyer, S.; Humblet, C. G-Protein Coupled Receptors: Models, Mutagenesis, and Drug Design. J. Med. Chem. 1998, 41, 2911-2927.
    • (1998) J. Med. Chem. , vol.41 , pp. 2911-2927
    • Bikker, J.A.1    Trumpp-Kallmeyer, S.2    Humblet, C.3
  • 2
    • 0038102324 scopus 로고    scopus 로고
    • The Evolutionary Triumphant G-Protein-Coupled Receptor
    • Perez, D. M. The Evolutionary Triumphant G-Protein-Coupled Receptor. Mol. Pharmacol. 2003, 63, 1202-1205.
    • (2003) Mol. Pharmacol. , vol.63 , pp. 1202-1205
    • Perez, D.M.1
  • 3
    • 0037247895 scopus 로고    scopus 로고
    • GPCRs come of age in San Diego
    • Crossley, R. GPCRs come of age in San Diego. Drug Discovery Today 2003, 8, 19-20.
    • (2003) Drug Discovery Today , vol.8 , pp. 19-20
    • Crossley, R.1
  • 4
    • 0035083109 scopus 로고    scopus 로고
    • Inverse, protean, and ligand-selective agonism: Matters of receptor conformation
    • Kenakin, T. Inverse, protean, and ligand-selective agonism: matters of receptor conformation. FASEB J. 2001, 15, 598-611.
    • (2001) FASEB J. , vol.15 , pp. 598-611
    • Kenakin, T.1
  • 6
    • 0036033424 scopus 로고    scopus 로고
    • Constitutive activity of G-protein-coupled receptor: Cause of disease and common property of wild type receptors
    • (b) Seifert, R.; Wenzel-Seifert, K. Constitutive activity of G-protein-coupled receptor: cause of disease and common property of wild type receptors. Naunyn-Schmiedeberg's Arch. Pharmacol. 2002, 366, 381-416.
    • (2002) Naunyn-Schmiedeberg's Arch. Pharmacol. , vol.366 , pp. 381-416
    • Seifert, R.1    Wenzel-Seifert, K.2
  • 7
    • 0032541084 scopus 로고    scopus 로고
    • G Protein-Coupled Receptors II. Mechanism of Agonist Activation
    • Gether, U.; Koblika, B. K. G Protein-Coupled Receptors II. Mechanism of Agonist Activation. J. Biol. Chem. 1998, 273, 17979-17982.
    • (1998) J. Biol. Chem. , vol.273 , pp. 17979-17982
    • Gether, U.1    Koblika, B.K.2
  • 8
    • 0032723795 scopus 로고    scopus 로고
    • Dopamine D4/D2 Receptor Selectivity Is Determined by a Divergent Aromatic Microdomain Contained within the Second, Third, and Seventh Membrane-Spanning Segments
    • (a) Simpson, M. M.; Ballesteros, J. A.; Chiappa, V.; Chen, J.; Suehiro, M.; Hartman, D. S.; Godel, T.; Snyder, L. A.; Sakmar, T. P.; Javitch, J. A. Dopamine D4/D2 Receptor Selectivity Is Determined by a Divergent Aromatic Microdomain Contained within the Second, Third, and Seventh Membrane-Spanning Segments. Mol. Pharmacol. 1999, 56, 116-1126.
    • (1999) Mol. Pharmacol. , vol.56 , pp. 116-1126
    • Simpson, M.M.1    Ballesteros, J.A.2    Chiappa, V.3    Chen, J.4    Suehiro, M.5    Hartman, D.S.6    Godel, T.7    Snyder, L.A.8    Sakmar, T.P.9    Javitch, J.A.10
  • 9
    • 0033982868 scopus 로고    scopus 로고
    • 4 Dopamine Receptor Are Molecular Determinants of D4 Selective Pharmacology
    • 4 Dopamine Receptor Are Molecular Determinants of D4 Selective Pharmacology. Mol. Pharmacol. 2000, 57, 144-152.
    • (2000) Mol. Pharmacol. , vol.57 , pp. 144-152
    • Schetz, J.A.1    Benjamin, P.S.2    Sibley, D.R.3
  • 13
    • 0032480988 scopus 로고    scopus 로고
    • N-n-Propyl-Substituted 3-(Dimethylphenyl)piperidines Display Novel Discriminative Properties between Dopamine Receptor Subtypes: Synthesis and Receptor Binding Studies
    • (d) Cervetto, L.; Demonthis, G. C.; Giannaccini, G.; Longoni, B.; Macchia, B.; Macchia, M.; Martinelli, A.; Orlandini, E. N-n-Propyl-Substituted 3-(Dimethylphenyl)piperidines Display Novel Discriminative Properties between Dopamine Receptor Subtypes: Synthesis and Receptor Binding Studies. J. Med. Chem. 1998, 41, 4933-4938.
    • (1998) J. Med. Chem. , vol.41 , pp. 4933-4938
    • Cervetto, L.1    Demonthis, G.C.2    Giannaccini, G.3    Longoni, B.4    Macchia, B.5    Macchia, M.6    Martinelli, A.7    Orlandini, E.8
  • 15
    • 0036169280 scopus 로고    scopus 로고
    • The Binding Site of Aminergic G-Protein-Coupled Receptors: The Transmembrane Segments and Second Extracellular Loop
    • Shi, L.; Javitch, J. A. The Binding Site of Aminergic G-Protein-Coupled Receptors: The Transmembrane Segments and Second Extracellular Loop. Annu. Rev. Pharmacol. Toxicol. 2002, 42, 437-467
    • (2002) Annu. Rev. Pharmacol. Toxicol. , vol.42 , pp. 437-467
    • Shi, L.1    Javitch, J.A.2
  • 16
    • 0032504237 scopus 로고    scopus 로고
    • G Protein-Coupled Receptors. I. Diversity of Receptor-Ligand Interactions
    • Ji, T. H.; Grossmann, M.; Ji, I. G Protein-Coupled Receptors. I. Diversity of Receptor-Ligand Interactions. J. Biol. Chem. 1998, 273, 17299-17302.
    • (1998) J. Biol. Chem. , vol.273 , pp. 17299-17302
    • Ji, T.H.1    Grossmann, M.2    Ji, I.3
  • 17
    • 0034684250 scopus 로고    scopus 로고
    • Natural Product-like Combinatorial Libraries Based on Privledged Structures. 1. General Principles and Solid Phase Synthesis of Benzopyrans
    • (a) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barluenga, S.; Mitchell, H. J. Natural Product-like Combinatorial Libraries Based on Privledged Structures. 1. General Principles and Solid Phase Synthesis of Benzopyrans. J. Am. Chem. Soc. 2000, 122, 9939-9953.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 9939-9953
    • Nicolaou, K.C.1    Pfefferkorn, J.A.2    Roecker, A.J.3    Cao, G.-Q.4    Barluenga, S.5    Mitchell, H.J.6
  • 18
    • 0042121318 scopus 로고    scopus 로고
    • Medicinal chemistry of target family-directed masterkeys
    • (b) Muller, G. Medicinal chemistry of target family-directed masterkeys. Drug Discovery Today 2003, 8, 681-691.
    • (2003) Drug Discovery Today , vol.8 , pp. 681-691
    • Muller, G.1
  • 19
    • 0032829657 scopus 로고    scopus 로고
    • Dopamine receptors-physiological understanding to therapeutic intervention potential
    • Emilien, G.; Maloteaux, J.-M.; Geurts, M.; Hoogenberg, K.; Cragg, S. Dopamine receptors-physiological understanding to therapeutic intervention potential. Pharmacol. Ther. 1999, 84, 133-156.
    • (1999) Pharmacol. Ther. , vol.84 , pp. 133-156
    • Emilien, G.1    Maloteaux, J.-M.2    Geurts, M.3    Hoogenberg, K.4    Cragg, S.5
  • 20
    • 0033915001 scopus 로고    scopus 로고
    • 4 receptor: A controversial therapeutic target
    • 4 receptor: a controversial therapeutic target. Drugs Future 2000, 25, 587-611.
    • (2000) Drugs Future , vol.25 , pp. 587-611
    • Hrib, N.J.1
  • 23
    • 0035899181 scopus 로고    scopus 로고
    • Rational Based Efficacy Tunning of Selective Dopamine D4 Receptor Ligands Leading to the Complete Antagonist 2-[4-(4-Chlorophenyl)-piperazin-1-ylmethyl]pyrazolo[1,5-a]pyridine (FAUC 213)
    • Lober, S.; Hubner, H.; Utz, W.; Gmeiner, P. Rational Based Efficacy Tunning of Selective Dopamine D4 Receptor Ligands Leading to the Complete Antagonist 2-[4-(4-Chlorophenyl)-piperazin-1-ylmethyl]pyrazolo[1,5-a]pyridine (FAUC 213). J. Med. Chem. 2001, 44, 2691-2694.
    • (2001) J. Med. Chem. , vol.44 , pp. 2691-2694
    • Lober, S.1    Hubner, H.2    Utz, W.3    Gmeiner, P.4
  • 29
    • 0037333504 scopus 로고    scopus 로고
    • RO-10-5824 is a selective dopamine D4 receptor agonist that increases novel object exploration in C57 mice
    • (c) Powell, S. B.; Paulus, M. P.; Hartman, D. S.; Godel, T.; Geyer, M. A. RO-10-5824 is a selective dopamine D4 receptor agonist that increases novel object exploration in C57 mice. Neuropharmacology 2003, 44, 473-481.
    • (2003) Neuropharmacology , vol.44 , pp. 473-481
    • Powell, S.B.1    Paulus, M.P.2    Hartman, D.S.3    Godel, T.4    Geyer, M.A.5
  • 30
    • 0242386506 scopus 로고    scopus 로고
    • Binding Affinities of Host-Guest, Protein-Ligand, and Protein-Transition-State Complexes
    • (a) Houk, K. N.; Leach, A. G.; Kim, S. P.; Zhang, X. Binding Affinities of Host-Guest, Protein-Ligand, and Protein-Transition-State Complexes. Angew. Chem., Int. Ed. 2003, 42, 4872-4897.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 4872-4897
    • Houk, K.N.1    Leach, A.G.2    Kim, S.P.3    Zhang, X.4
  • 31
    • 33751157207 scopus 로고
    • Enthalpy-Entropy Compensation in Drug-Receptor Binding
    • (b) Gilli, P.; Ferretti, V.; Gilli, G.; Borea, P. A. Enthalpy-Entropy Compensation in Drug-Receptor Binding. J. Phys. Chem. 1994, 98, 1515-1518.
    • (1994) J. Phys. Chem. , vol.98 , pp. 1515-1518
    • Gilli, P.1    Ferretti, V.2    Gilli, G.3    Borea, P.A.4
  • 32
    • 0024496899 scopus 로고
    • Thermodynamic Analysis of the Drug-Receptor Interaction
    • (c) Raffa, R. B.; Porreca, F. Thermodynamic Analysis of the Drug-Receptor Interaction. Life Sci. 1989, 44, 245-258.
    • (1989) Life Sci. , vol.44 , pp. 245-258
    • Raffa, R.B.1    Porreca, F.2
  • 35
    • 0033151694 scopus 로고    scopus 로고
    • Chimeric G Proteins Allow a High-Throughput Signaling Assay of G-Coupled Receptors
    • (b) Coward, P.; Chan, S. D. H.; Wada, H. G.; Humphries, G. M.; Conklin, B. R. Chimeric G Proteins Allow a High-Throughput Signaling Assay of G-Coupled Receptors. Anal. Biochem. 1999, 270, 242-248.
    • (1999) Anal. Biochem. , vol.270 , pp. 242-248
    • Coward, P.1    Chan, S.D.H.2    Wada, H.G.3    Humphries, G.M.4    Conklin, B.R.5
  • 38
    • 36148959779 scopus 로고    scopus 로고
    • The use of bioisoteric groups in lead optimization
    • (b) Chen, X.; Wang, W. The use of bioisoteric groups in lead optimization. Annu. Rep. Med. Chem. 2003, 38, 333-346.
    • (2003) Annu. Rep. Med. Chem. , vol.38 , pp. 333-346
    • Chen, X.1    Wang, W.2
  • 39
    • 0019422355 scopus 로고
    • A Practioner's Perspective of the Role of Quantitative Structure-Activity Analysis in Medicinal Chemistry
    • (c) Martin, Y. C. A Practioner's Perspective of the Role of Quantitative Structure-Activity Analysis in Medicinal Chemistry. J. Med. Chem. 1981, 24, 229-237.
    • (1981) J. Med. Chem. , vol.24 , pp. 229-237
    • Martin, Y.C.1
  • 40
    • 0032199006 scopus 로고    scopus 로고
    • Binding, gating, affinity, and efficacy: The interpretation of structure-activity relationships for agonists and of the effects of mutating receptors
    • (a) Colquoun, D. Binding, gating, affinity, and efficacy: The interpretation of structure-activity relationships for agonists and of the effects of mutating receptors. Br. J. Pharmacol. 1998, 125, 924-947.
    • (1998) Br. J. Pharmacol. , vol.125 , pp. 924-947
    • Colquoun, D.1
  • 41
    • 0028950255 scopus 로고
    • The two-state model of receptor activation
    • (b) Leff, P. The two-state model of receptor activation. Trends Pharmacol. Sci. 1995, 16, 89-97.
    • (1995) Trends Pharmacol. Sci. , vol.16 , pp. 89-97
    • Leff, P.1
  • 43
    • 0017671339 scopus 로고
    • Slowly Reversible Binding of Catecholamine to a Nucleotide-Sensitive State of the β-Adrenergic Receptor
    • Williams, L. T.; Lefkowitz, R. J. Slowly Reversible Binding of Catecholamine to a Nucleotide-Sensitive State of the β-Adrenergic Receptor. J. Biol. Chem. 1977, 252, 7207-7213.
    • (1977) J. Biol. Chem. , vol.252 , pp. 7207-7213
    • Williams, L.T.1    Lefkowitz, R.J.2
  • 47
    • 0031037070 scopus 로고    scopus 로고
    • Noradrenaline and adrenaline are high affinity agonists at dopamine D4 receptors
    • Newman-Tancredi, A.; Audinot-Bouchez, V.; Gobert, A.; Millan, M. J. Noradrenaline and adrenaline are high affinity agonists at dopamine D4 receptors. Eur. J. Pharmacol. 1997, 319, 379-383.
    • (1997) Eur. J. Pharmacol. , vol.319 , pp. 379-383
    • Newman-Tancredi, A.1    Audinot-Bouchez, V.2    Gobert, A.3    Millan, M.J.4
  • 48
    • 0027049395 scopus 로고
    • Intrinsic Activity Determinations at the Dopamine D2 Guanine Nucleotide-Binding Protein-Coupled Receptor: Utilization of Receptor State Binding Affinities
    • (a) Lahti, R. A.; Figur, L. M.; Piercey, M. F.; Ruppel, P. L.; Evans, D. L. Intrinsic Activity Determinations at the Dopamine D2 Guanine Nucleotide-Binding Protein-Coupled Receptor: Utilization of Receptor State Binding Affinities. Mol. Pharmacol. 1992, 42, 432-438.
    • (1992) Mol. Pharmacol. , vol.42 , pp. 432-438
    • Lahti, R.A.1    Figur, L.M.2    Piercey, M.F.3    Ruppel, P.L.4    Evans, D.L.5
  • 51
    • 0037452545 scopus 로고    scopus 로고
    • A Conformational Trigger for Activation of a G protein by a G Protein-Coupled Receptor
    • (a) Yeagle, P. L.; Albert, A. D. A Conformational Trigger for Activation of a G protein by a G Protein-Coupled Receptor. Biochem. 2003, 42, 1365-1368.
    • (2003) Biochem. , vol.42 , pp. 1365-1368
    • Yeagle, P.L.1    Albert, A.D.2
  • 52
    • 0032897494 scopus 로고    scopus 로고
    • An analysis of conformational changes on protein-protein association: Implications for predictive docking
    • (b) Betts, J. B.; Sternberg, M. J. E. An analysis of conformational changes on protein-protein association: implications for predictive docking. Protein Eng. 1999, 12, 271-283.
    • (1999) Protein Eng. , vol.12 , pp. 271-283
    • Betts, J.B.1    Sternberg, M.J.E.2
  • 54
    • 0004135644 scopus 로고
    • W. H. Freeman and Company: San Fransisco
    • Walsh, C. Enzymatic Reaction Mechanisms; W. H. Freeman and Company: San Fransisco, 1979; pp 33-35.
    • (1979) Enzymatic Reaction Mechanisms , pp. 33-35
    • Walsh, C.1
  • 56
    • 1542554559 scopus 로고
    • Effect of Conformational Change on Reactivity in Organic Chemistry. Evaluations, Applications, and Extensions of Curtin-Hammett/Winstein-Holness Kinetics
    • (b) Seeman, J. I. Effect of Conformational Change on Reactivity in Organic Chemistry. Evaluations, Applications, and Extensions of Curtin-Hammett/Winstein-Holness Kinetics. Chem. Rev. 1983, 83, 83-134.
    • (1983) Chem. Rev. , vol.83 , pp. 83-134
    • Seeman, J.I.1
  • 57
    • 0000151210 scopus 로고
    • Structural requirements for time-dependent inhibition of prostaglandin biosynthesis by antiinflammatory drugs
    • (a) Rome, L. H.; Lands, W. E. M. Structural requirements for time-dependent inhibition of prostaglandin biosynthesis by antiinflammatory drugs. Proc. Natl. Acad. Sci. U.S.A. 1975, 72, 4863-4865.
    • (1975) Proc. Natl. Acad. Sci. U.S.A. , vol.72 , pp. 4863-4865
    • Rome, L.H.1    Lands, W.E.M.2
  • 60
    • 0035497743 scopus 로고    scopus 로고
    • 16 the optimal tool for fishing ligands of orphan G-protein-coupled receptors?
    • 16 the optimal tool for fishing ligands of orphan G-protein-coupled receptors? Trends Pharmacol. Sci. 2001, 22, 560-564.
    • (2001) Trends Pharmacol. Sci. , vol.22 , pp. 560-564
    • Kostenis, E.1
  • 61
    • 0037794320 scopus 로고    scopus 로고
    • Predicting Therapeutic Value in the Lead Optimization Phase of Drug Discovery
    • Kenakin, T. Predicting Therapeutic Value in the Lead Optimization Phase of Drug Discovery. Nat. Rev. Drug Discovery 2003, 2, 429-438.
    • (2003) Nat. Rev. Drug Discovery , vol.2 , pp. 429-438
    • Kenakin, T.1


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