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Volumn 41, Issue 11, 1998, Pages 1980-1990

Investigation of the N-substituent conformation governing potency and μ receptor subtype-selectivity in (+)-(3R,4R)-dimethyl-4-(3- hydroxyphenyl)piperidine opioid antagonists

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUP; N (4 PHENYL 2 BUTENYL)DIMETHYL 4 (3 HYDROXYPHENYL)PIPERIDINE FUMARATE; N [(2 CHLOROPHENYL) 2 BUTENYL]DIMETHYL 4 (3 HYDROXYPHENYL)PIPERIDINE FUMARATE; OPIATE ANTAGONIST; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 15444345625     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980063g     Document Type: Article
Times cited : (38)

References (27)
  • 1
    • 0001911108 scopus 로고
    • Opioid Receptors
    • Emmett, J. C., Ed.; Pergamon: Oxford
    • Rees, D. C.; Hunter, J. C. Opioid Receptors. In Comprehensive Medicinal Chemistry, Emmett, J. C., Ed.; Pergamon: Oxford, 1990; Vol. 3, pp 805-846.
    • (1990) Comprehensive Medicinal Chemistry , vol.3 , pp. 805-846
    • Rees, D.C.1    Hunter, J.C.2
  • 2
    • 0003799353 scopus 로고    scopus 로고
    • Wolff, M. E., Ed.; John Wiley & Sons: Inc.: New York, Therapeutic Agents
    • Aldrich, J. V. Analgesics. In Burger's Medicinal Chemistry and Drug Discovery, Wolff, M. E., Ed.; John Wiley & Sons: Inc.: New York, 1996; Vol. 3, Therapeutic Agents.
    • (1996) Burger's Medicinal Chemistry and Drug Discovery , vol.3
    • Analgesics, A.J.V.1
  • 3
    • 15444342307 scopus 로고
    • Binaltorphimine-related bivalent ligands and their κ opioid receptor antagonist selectivity published erratum appears
    • Portoghese, P. S.; Nagase, H.; Lipkowski, A. W.; Larson, D. L.; Takemori, A. E. Binaltorphimine-related bivalent ligands and their κ opioid receptor antagonist selectivity [published erratum appears in J. Med. Chem. 1988, 31, 2056]. J. Med. Chem. 1988, 31, 836-841.
    • (1988) J. Med. Chem. , vol.31 , pp. 2056
    • Portoghese, P.S.1    Nagase, H.2    Lipkowski, A.W.3    Larson, D.L.4    Takemori, A.E.5
  • 4
    • 0023889865 scopus 로고
    • Portoghese, P. S.; Nagase, H.; Lipkowski, A. W.; Larson, D. L.; Takemori, A. E. Binaltorphimine-related bivalent ligands and their κ opioid receptor antagonist selectivity [published erratum appears in J. Med. Chem. 1988, 31, 2056]. J. Med. Chem. 1988, 31, 836-841.
    • (1988) J. Med. Chem. , vol.31 , pp. 836-841
  • 5
    • 0025895073 scopus 로고
    • Role of spacer and address components in peptidomimetic δ opioid receptor antagonists related to naltrindole
    • Portoghese, P. S.; Nagase, H.; Maloneyhuss, K. E.; Lin, C. E.; Takemori, A. E. Role of spacer and address components in peptidomimetic δ opioid receptor antagonists related to naltrindole. J. Med. Chem. 1991, 34, 1715-1720.
    • (1991) J. Med. Chem. , vol.34 , pp. 1715-1720
    • Portoghese, P.S.1    Nagase, H.2    Maloneyhuss, K.E.3    Lin, C.E.4    Takemori, A.E.5
  • 6
    • 0028590201 scopus 로고
    • κ Opioid receptor selective affinity labels: Electrophilic benzeneacetamides as κ-selective opioid antagonists
    • Chang, A.-C.; Takemori, A. E.; Qjala, W. H.; Gleason, W. B.; Portoghese, P. S. κ Opioid receptor selective affinity labels: Electrophilic benzeneacetamides as κ-selective opioid antagonists. J. Med. Chem. 1994, 37, 4490-4498.
    • (1994) J. Med. Chem. , vol.37 , pp. 4490-4498
    • Chang, A.-C.1    Takemori, A.E.2    Qjala, W.H.3    Gleason, W.B.4    Portoghese, P.S.5
  • 7
    • 0018135396 scopus 로고
    • New structural concepts for narcotic antagonists defined in a 4-phenylpiperidine series
    • Zimmerman, D. M.; Nickander, R.; Horng, J. S.; Wong, D. T. New structural concepts for narcotic antagonists defined in a 4-phenylpiperidine series. Nature 1978, 275, 332-334.
    • (1978) Nature , vol.275 , pp. 332-334
    • Zimmerman, D.M.1    Nickander, R.2    Horng, J.S.3    Wong, D.T.4
  • 8
    • 0025232625 scopus 로고
    • Selective opioid receptor agonists and antagonists: Research tools and potential therapeutic agents
    • Zimmerman, D. M.; Leander, J. D. Selective opioid receptor agonists and antagonists: Research tools and potential therapeutic agents. J. Med. Chem. 1990, 33, 895-902.
    • (1990) J. Med. Chem. , vol.33 , pp. 895-902
    • Zimmerman, D.M.1    Leander, J.D.2
  • 9
    • 0027448954 scopus 로고
    • Structure-activity relationships of the trans-3,4-dimethyl-4-(3-hydroxypheny)piperidine antagonists for μ and κ opioid receptors
    • Zimmerman, D. M.; Leander, J. D.; Cantrell, B. E.; Reel, J. K.; Snoddy, J.; Mendelsohn, L. G.; Johnson, B. G.; Mitch, C. H. Structure-activity relationships of the trans-3,4-dimethyl-4-(3-hydroxypheny)piperidine antagonists for μ and κ opioid receptors. J. Med. Chem. 1993, 36, 2833-2841.
    • (1993) J. Med. Chem. , vol.36 , pp. 2833-2841
    • Zimmerman, D.M.1    Leander, J.D.2    Cantrell, B.E.3    Reel, J.K.4    Snoddy, J.5    Mendelsohn, L.G.6    Johnson, B.G.7    Mitch, C.H.8
  • 10
    • 0012650371 scopus 로고
    • Piperidine derivatives. XXX. 1,4-Dialkyl-4-aryl piperidines
    • McElvain, S. M.; Clemens, D. H. Piperidine derivatives. XXX. 1,4-Dialkyl-4-aryl piperidines. J. Am. Chem. Soc. 1958, 80, 3915-3923.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 3915-3923
    • McElvain, S.M.1    Clemens, D.H.2
  • 14
    • 0025973653 scopus 로고
    • Synthesis and Absolute Configuration of LY255582, a potent opioid antagonist
    • Mitch, C. H.; Zimmerman, D. M.; Snoddy, J. D.; Reel, J. K.; Cantrell, B. E. Synthesis and Absolute Configuration of LY255582, a potent opioid antagonist. J. Org. Chem. 1991, 56, 1660-1663.
    • (1991) J. Org. Chem. , vol.56 , pp. 1660-1663
    • Mitch, C.H.1    Zimmerman, D.M.2    Snoddy, J.D.3    Reel, J.K.4    Cantrell, B.E.5
  • 15
    • 0027930289 scopus 로고
    • Discovery of a potent, peripherally selective trans-3,4-dimethyl-4-(3-hydroxyphenyl)-piperidine opioid antagonist for the treatment of gastrointestinal motility disorders
    • Zimmerman, D. M.; Gidda, J. S.; Cantrell, B. E.; Schoepp, D. D.; Johnson, B. G.; Leander, J. D. Discovery of a potent, peripherally selective trans-3,4-dimethyl-4-(3-hydroxyphenyl)-piperidine opioid antagonist for the treatment of gastrointestinal motility disorders. J. Med. Chem. 1994, 37, 2262-2265.
    • (1994) J. Med. Chem. , vol.37 , pp. 2262-2265
    • Zimmerman, D.M.1    Gidda, J.S.2    Cantrell, B.E.3    Schoepp, D.D.4    Johnson, B.G.5    Leander, J.D.6
  • 19
    • 0027444691 scopus 로고
    • A single residue, aspartic acid 95, in the δ opioid receptor specifies selective high affinity agonist binding
    • Kong, H.; Raynor, K.; Yasuda, K.; Moe, S. T.; Portoghese, P. S.; Bell, G. I.; Reisine, T. A single residue, aspartic acid 95, in the δ opioid receptor specifies selective high affinity agonist binding. J. Biol. Chem. 1993, 268, 23055-23058.
    • (1993) J. Biol. Chem. , vol.268 , pp. 23055-23058
    • Kong, H.1    Raynor, K.2    Yasuda, K.3    Moe, S.T.4    Portoghese, P.S.5    Bell, G.I.6    Reisine, T.7
  • 21
    • 0030028469 scopus 로고    scopus 로고
    • Synthesis, biological evaluation, and quantitative receptor docking simulations of 2-[(acylamino)ethyl]-1,4-benzodiazepines as novel tifluadom-like ligands with high affinity and selectivity for κ-opioid receptors
    • Cappelli, A.; Anzini, M.; Vomero, S.; Menziani, M. C.; De Benedetti, P. G.; Sbacchi, M.; Clarke, G. D.; Mennuni, L. Synthesis, biological evaluation, and quantitative receptor docking simulations of 2-[(acylamino)ethyl]-1,4-benzodiazepines as novel tifluadom-like ligands with high affinity and selectivity for κ-opioid receptors. J. Med. Chem. 1996, 39, 860-872.
    • (1996) J. Med. Chem. , vol.39 , pp. 860-872
    • Cappelli, A.1    Anzini, M.2    Vomero, S.3    Menziani, M.C.4    De Benedetti, P.G.5    Sbacchi, M.6    Clarke, G.D.7    Mennuni, L.8
  • 22
    • 0027460624 scopus 로고
    • A single amino acid of the cholecystokinin-B/gastrin receptor determines specificity for non-peptide antagonists
    • Beinborn, M.; Lee, Y. M.; McBride, E. W.; Quinn, S. M.; Kopin, A. S. A single amino acid of the cholecystokinin-B/gastrin receptor determines specificity for non-peptide antagonists. Nature 1993, 362, 348-350.
    • (1993) Nature , vol.362 , pp. 348-350
    • Beinborn, M.1    Lee, Y.M.2    McBride, E.W.3    Quinn, S.M.4    Kopin, A.S.5
  • 23
    • 0025256967 scopus 로고
    • Interaction of endogenous opioid peptides and other drugs with four κ opioid binding sites in guinea pig brain
    • Rothman, R. B.; Bykov, V.; de Costa, B. R.; Jacobson, A. E.; Rice, K. C.; Brady, L. S. Interaction of endogenous opioid peptides and other drugs with four κ opioid binding sites in guinea pig brain Peptides 1990, 11, 311-331.
    • (1990) Peptides , vol.11 , pp. 311-331
    • Rothman, R.B.1    Bykov, V.2    De Costa, B.R.3    Jacobson, A.E.4    Rice, K.C.5    Brady, L.S.6
  • 24
    • 0001104895 scopus 로고
    • Kinetics of the decarboxylative elimination of cinnamic acid dibromides
    • Trumbull, E. R.; Finn, R. T.; Ibne-Rasa, K. M.; Sauere, C. K. Kinetics of the decarboxylative elimination of cinnamic acid dibromides. J. Org. Chem. 1962, 27, 2339-2344.
    • (1962) J. Org. Chem. , vol.27 , pp. 2339-2344
    • Trumbull, E.R.1    Finn, R.T.2    Ibne-Rasa, K.M.3    Sauere, C.K.4
  • 25
    • 0345029382 scopus 로고
    • Cis-2-Phenylcyclopropanecarboxylic acid (cyclopropanecarboxylic acid, 2-phenyl-, cis-)
    • Kaiser, C.; Weinstock, J.; Olmstead, M. P. cis-2-Phenylcyclopropanecarboxylic acid (cyclopropanecarboxylic acid, 2-phenyl-, cis-). Org. Synth. 1988, VI, 913-915.
    • (1988) Org. Synth. , vol.6 , pp. 913-915
    • Kaiser, C.1    Weinstock, J.2    Olmstead, M.P.3
  • 26
    • 0025729102 scopus 로고
    • RTI-4614-4: An analog of (+)-cis-3-methylfentanyl with a 27,000-fold binding selectivity for μ versus δ opioid binding sites
    • Rothman, R. B.; Xu, H.; Seggel, M.; Jacobson, A. E.; Rice, K. C.; Brine, G. A.; Carroll, F. I. RTI-4614-4: an analog of (+)-cis-3-methylfentanyl with a 27,000-fold binding selectivity for μ versus δ opioid binding sites. Life Sci. 1991, 48, PL111-PL116.
    • (1991) Life Sci. , vol.48
    • Rothman, R.B.1    Xu, H.2    Seggel, M.3    Jacobson, A.E.4    Rice, K.C.5    Brine, G.A.6    Carroll, F.I.7
  • 27
    • 0017250843 scopus 로고
    • Statistical characterization of the random errors in the radioimmunoassay dose-response variable
    • Rodbard, D.; Lenox, R. H.; Wray, H. L.; Ramseth, D. Statistical characterization of the random errors in the radioimmunoassay dose-response variable. Clin. Chem. 1976, 22, 350-358.
    • (1976) Clin. Chem. , vol.22 , pp. 350-358
    • Rodbard, D.1    Lenox, R.H.2    Wray, H.L.3    Ramseth, D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.