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Volumn 39, Issue 18, 1996, Pages 3564-3568

Synthesis and evaluation of aryl-substituted N-(arylethyl)-N-methyl-2- (1-pyrrolidinyl)ethylamines and corresponding arylacetamides for sigma receptor affinity

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; DEXTRALLORPHAN; ETHYLENEDIAMINE DERIVATIVE; HALOPERIDOL; PENTAZOCINE; SIGMA OPIATE RECEPTOR;

EID: 0029815434     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9600813     Document Type: Article
Times cited : (13)

References (32)
  • 1
    • 0023952339 scopus 로고
    • Evidence for a role of haloperidol-sensitive sigma opiate receptors in the motor effects of antip-sychotic drugs
    • Walker, J. M.; Matsumoto, R. R.; Bowen, W. D.; Gans, D. L.; Jones, K. D.; Walker, F. O. Evidence for a role of haloperidol-sensitive sigma opiate receptors in the motor effects of antip-sychotic drugs. Neurology 1988, 38, 961-965.
    • (1988) Neurology , vol.38 , pp. 961-965
    • Walker, J.M.1    Matsumoto, R.R.2    Bowen, W.D.3    Gans, D.L.4    Jones, K.D.5    Walker, F.O.6
  • 4
    • 0023918128 scopus 로고
    • Sigma receptors negatively modulate agonist-stimulated phosphoinositide metabolism in rat brain
    • Bowen, W. D.; Kirschner, B. N.; Newman, A. H.; Rice, K. C. Sigma receptors negatively modulate agonist-stimulated phosphoinositide metabolism in rat brain. Eur. J. Pharmacol. 1988, 149, 399-400.
    • (1988) Eur. J. Pharmacol. , vol.149 , pp. 399-400
    • Bowen, W.D.1    Kirschner, B.N.2    Newman, A.H.3    Rice, K.C.4
  • 5
    • 0002646058 scopus 로고
    • Inhibition of the cholinergic phosphoinositide response by sigma ligands: Distinguishing a sigma receptor-mediated mechanism from a mechanism involving direct cholinergic antagonism
    • Kamenka, J.-M., Domino, E. F., Eds.; NPP Books: Ann Arbor, MI
    • Bowen, W. D.; Tolentino, P. J.; Hsu, K. K.; Cutts, J. M.; Naidu, S.S. Inhibition of the cholinergic phosphoinositide response by sigma ligands: Distinguishing a sigma receptor-mediated mechanism from a mechanism involving direct cholinergic antagonism. Multiple Sigma and PCP Receptor Ligands: Mechanisms for Neuromodulation and Neuroprotection; Kamenka, J.-M., Domino, E. F., Eds.; NPP Books: Ann Arbor, MI, 1992, pp 155-167.
    • (1992) Multiple Sigma and PCP Receptor Ligands: Mechanisms for Neuromodulation and Neuroprotection , pp. 155-167
    • Bowen, W.D.1    Tolentino, P.J.2    Hsu, K.K.3    Cutts, J.M.4    Naidu, S.S.5
  • 6
    • 0026650831 scopus 로고
    • In vivo electrophysiological evidence for a selective modulation of N-methyl-D-aspartate-induced neuronal activation in rat CA3 dorsal hippocampus by sigma ligands
    • (a) Monnet, F. P.; Debonnel, G.; de Montigny, C. In vivo electrophysiological evidence for a selective modulation of N-methyl-D-aspartate-induced neuronal activation in rat CA3 dorsal hippocampus by sigma ligands. J. Pharmacol. Exp. Ther. 1992, 261, 123-130.
    • (1992) J. Pharmacol. Exp. Ther. , vol.261 , pp. 123-130
    • Monnet, F.P.1    Debonnel, G.2    De Montigny, C.3
  • 7
    • 0028171131 scopus 로고
    • 3H]dopamine release from rat striatal slices by sigma receptor ligands
    • 3H]dopamine release from rat striatal slices by sigma receptor ligands. J. Pharmacol. Ther. 1994, 271, 212-219.
    • (1994) J. Pharmacol. Ther. , vol.271 , pp. 212-219
    • Gonzalez-Alvear, G.M.1    Werling, L.L.2
  • 8
    • 0023256145 scopus 로고
    • Guinea pig vas deferens preparation may contain both sigma receptors and phencyclidine receptors
    • Vaupel, D. B.; Su, T. P. Guinea pig vas deferens preparation may contain both sigma receptors and phencyclidine receptors. Eur. J. Pharmacol. 1987, 139, 125-128.
    • (1987) Eur. J. Pharmacol. , vol.139 , pp. 125-128
    • Vaupel, D.B.1    Su, T.P.2
  • 9
    • 0025346865 scopus 로고
    • Multiple vascular effects of Sigma and PCP ligands. Inhibition of amine uptake and contractile responses
    • Massamiri, T.; Duckles, S. P. Multiple vascular effects of Sigma and PCP ligands. Inhibition of amine uptake and contractile responses. J. Pharmacol. Exp. Ther. 1990, 253, 124-129.
    • (1990) J. Pharmacol. Exp. Ther. , vol.253 , pp. 124-129
    • Massamiri, T.1    Duckles, S.P.2
  • 10
    • 0011196931 scopus 로고
    • Selective sigma ligands protect aginst dynorphin A-induced spinal cord injury in rats
    • abstr. 461.4
    • Long, J. B.; Tidwell, R. E.; Tortella, F. C.; Rice, K. C.; de Costa, B. R. Selective sigma ligands protect aginst dynorphin A-induced spinal cord injury in rats. Soc. Neurosci. Abstr. 1990, 16, 1122, abstr. 461.4.
    • (1990) Soc. Neurosci. Abstr. , vol.16 , pp. 1122
    • Long, J.B.1    Tidwell, R.E.2    Tortella, F.C.3    Rice, K.C.4    De Costa, B.R.5
  • 12
    • 0027471841 scopus 로고
    • Sigma receptor-active neuroleptics are cytotoxic to C6 glioma cells in culture
    • Vilner, B. J.; Bowen, W. D. Sigma receptor-active neuroleptics are cytotoxic to C6 glioma cells in culture. Eur, J. Pharmacol., Mol. Pharmacol. Sect. 1993, 244, 199-201.
    • (1993) Eur, J. Pharmacol., Mol. Pharmacol. Sect. , vol.244 , pp. 199-201
    • Vilner, B.J.1    Bowen, W.D.2
  • 13
    • 0343282976 scopus 로고
    • Sigma receptor-mediated morphological and cytotoxic effects on primary cultures of rat central and peripheral nervous system
    • abstr. 314.10
    • Bowen, W. D.; Vilner, B. J. Sigma receptor-mediated morphological and cytotoxic effects on primary cultures of rat central and peripheral nervous system. Soc. Neurosci. Abstr. 1994, 20, 747, abstr. 314.10.
    • (1994) Soc. Neurosci. Abstr. , vol.20 , pp. 747
    • Bowen, W.D.1    Vilner, B.J.2
  • 14
    • 0028876578 scopus 로고
    • Cytotoxic effects of sigma ligands: Sigma receptor-mediated alterations in cellular morphology and viability
    • Vilner, B. J.; de Costa, B. R.; Bowen, W. D. Cytotoxic effects of sigma ligands: Sigma receptor-mediated alterations in cellular morphology and viability. J. Neurosci. 1995, 15, 117-134.
    • (1995) J. Neurosci. , vol.15 , pp. 117-134
    • Vilner, B.J.1    De Costa, B.R.2    Bowen, W.D.3
  • 16
    • 0025180755 scopus 로고
    • A sigma-like binding site in rat pheochromocytoma (PC12) cells: Decreased affinity for (+)-benzomorphans and lower molecular weight suggest a different sigma receptor form from that in guinea pig brain
    • Hellewell, S. B.; Bowen, W. D. A sigma-like binding site in rat pheochromocytoma (PC12) cells: Decreased affinity for (+)-benzomorphans and lower molecular weight suggest a different sigma receptor form from that in guinea pig brain. Brain Res. 1990, 527, 244-253.
    • (1990) Brain Res. , vol.527 , pp. 244-253
    • Hellewell, S.B.1    Bowen, W.D.2
  • 18
    • 0025131242 scopus 로고
    • Neuropeptide Y and J01784, a selective σ ligand, alter intestinal ion transport through a common, haloperidol-sensitive site
    • Riviere, P. J. M.; Pascaud, X.; Junien, J. L.; Porreca, F. Neuropeptide Y and J01784, a selective σ ligand, alter intestinal ion transport through a common, haloperidol-sensitive site. Eur. J. Pharmacol. 1980, 187, 557-559.
    • (1980) Eur. J. Pharmacol. , vol.187 , pp. 557-559
    • Riviere, P.J.M.1    Pascaud, X.2    Junien, J.L.3    Porreca, F.4
  • 19
    • 0025604167 scopus 로고
    • Effect of selective sigma ligands on duodenal alkaline secretion in the rat
    • Pascaud, X.; Defaux, J. P.; Roze, C.; Junien, J. L. Effect of selective sigma ligands on duodenal alkaline secretion in the rat. J. Pharmacol. Exp. Ther. 1990, 255, 1354-1359.
    • (1990) J. Pharmacol. Exp. Ther. , vol.255 , pp. 1354-1359
    • Pascaud, X.1    Defaux, J.P.2    Roze, C.3    Junien, J.L.4
  • 20
    • 0024427631 scopus 로고
    • Sigma receptors regulate contractions of the guinea-pig ileum longitudinal muscle/myenteric plexus preparation elicited by both electrical stimulation and exogenous serotonin
    • Campbell, B. G.; Scherz, M. W.; Keana, J. F. W.; Weber, E. Sigma receptors regulate contractions of the guinea-pig ileum longitudinal muscle/myenteric plexus preparation elicited by both electrical stimulation and exogenous serotonin. J. Neurosci. 1989, 9, 3380-3391.
    • (1989) J. Neurosci. , vol.9 , pp. 3380-3391
    • Campbell, B.G.1    Scherz, M.W.2    Keana, J.F.W.3    Weber, E.4
  • 22
    • 0026007022 scopus 로고
    • Electrophysiological and binding studies on intact NCB-20 cells suggest presence of a low affinity sigma receptor
    • (a) Wu, X. Z.; Bell, J. A.; Spivak, C. E.; London, E. D.; Su, T. P. Electrophysiological and binding studies on intact NCB-20 cells suggest presence of a low affinity sigma receptor. J. Pharmacol. Exp. Ther. 1991, 257, 351-359.
    • (1991) J. Pharmacol. Exp. Ther. , vol.257 , pp. 351-359
    • Wu, X.Z.1    Bell, J.A.2    Spivak, C.E.3    London, E.D.4    Su, T.P.5
  • 24
    • 0026575012 scopus 로고
    • Synthesis, characterization, and biological evaluation of a novel class of N-(arylethyl)-N-alkyl-2-(1-pyrrolidinyl)ethylamines: Structural requirements and binding affinity at the σ receptor
    • de Costa, B. R.; Radesca, L.; Di Paolo, L.; Bowen, W. D. Synthesis, characterization, and biological evaluation of a novel class of N-(arylethyl)-N-alkyl-2-(1-pyrrolidinyl)ethylamines: structural requirements and binding affinity at the σ receptor. J. Med. Chem. 1992, 35, 38-47.
    • (1992) J. Med. Chem. , vol.35 , pp. 38-47
    • De Costa, B.R.1    Radesca, L.2    Di Paolo, L.3    Bowen, W.D.4
  • 25
    • 0027462921 scopus 로고
    • Synthesis and binding characteristics of potential SPECT imaging agents for σ-1 and σ-2 binding sites
    • He, X. S.; Bowen, W. D.; Lee, K. S.; Williams, W.; Weinberger, D. R.; de Costa, B. R. Synthesis and binding characteristics of potential SPECT imaging agents for σ-1 and σ-2 binding sites. J. Med. Chem. 1993, 36, 566-572.
    • (1993) J. Med. Chem. , vol.36 , pp. 566-572
    • He, X.S.1    Bowen, W.D.2    Lee, K.S.3    Williams, W.4    Weinberger, D.R.5    De Costa, B.R.6
  • 26
    • 0343678156 scopus 로고
    • Benzimidazol-derivate und verwandte heterocyclen III Synthese von 1-aminoalkyl-2-benzyl-nitro-benzimidazolen
    • Hunger, von A.; Kebrle, J.; Rossi, A.; Hoffman, A. Benzimidazol-derivate und verwandte heterocyclen III) Synthese von 1-aminoalkyl-2-benzyl-nitro-benzimidazolen. Helv. Chim. Acta 1960, 43, 1032-1046.
    • (1960) Helv. Chim. Acta , vol.43 , pp. 1032-1046
    • Von Hunger, A.1    Kebrle, J.2    Rossi, A.3    Hoffman, A.4
  • 27
    • 0001377523 scopus 로고
    • Recent advances in the molecular pharmacology of benzodiazepine receptors and in the structure-activity relationships of their agonist
    • Haefely, W.; Kyburz, E.; Gerecke, M.; Mohler, H. Recent advances in the molecular pharmacology of benzodiazepine receptors and in the structure-activity relationships of their agonist. Adv. Drug Res. 1985, 14, 165-322.
    • (1985) Adv. Drug Res. , vol.14 , pp. 165-322
    • Haefely, W.1    Kyburz, E.2    Gerecke, M.3    Mohler, H.4
  • 28
    • 9544231357 scopus 로고    scopus 로고
    • note
    • 2).
  • 31
    • 0028180570 scopus 로고
    • Rat liver and kidney contain high densities of sigma-1 and sigma-2 receptors. Characterization by ligand binding and photoaffinity labeling
    • Hellewell, S. B.; Bruce, A.; Feinstein, G.; Orringer, J.; Williams, W.; Bowen, W. D. Rat liver and kidney contain high densities of sigma-1 and sigma-2 receptors. Characterization by ligand binding and photoaffinity labeling. Eur. J. Pharmacol., Mol. Pharmacol. Sect. 1994, 268, 9-18.
    • (1994) Eur. J. Pharmacol., Mol. Pharmacol. Sect. , vol.268 , pp. 9-18
    • Hellewell, S.B.1    Bruce, A.2    Feinstein, G.3    Orringer, J.4    Williams, W.5    Bowen, W.D.6
  • 32
    • 33947329803 scopus 로고
    • Selective Reductions. XII. Explorations in some representative applications of aluminum hydride for selective reductions
    • Yoon, N. M.; Brown, H. C. Selective Reductions. XII. Explorations in some representative applications of aluminum hydride for selective reductions. J. Am. Chem. Soc. 1968, 90, 2927-2938.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 2927-2938
    • Yoon, N.M.1    Brown, H.C.2


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