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Volumn 52, Issue 6, 2009, Pages 1553-1557

14β-O-cinnamoylnaltrexone and related dihydrocodeinones are mu opioid receptor partial agonists with predominant antagonist activity

Author keywords

[No Author keywords available]

Indexed keywords

14 CINNAMOYLAMINOMORPHINONE DERIVATIVE; 14BETA O CINNAMOYLNATREXONE; CINNAMOYLOXYCODEINONE DERIVATIVE; CINNAMOYLOXYMORPHINONE DERIVATIVE; HYDROCODONE DERIVATIVE; MORPHINE; MORPHINONE; MU OPIATE RECEPTOR; NALTREXONE; NALTRINDOLE; RECOMBINANT PROTEIN; UNCLASSIFIED DRUG;

EID: 64349089490     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8012272     Document Type: Article
Times cited : (13)

References (19)
  • 1
    • 0000383465 scopus 로고    scopus 로고
    • Schuster. C. R, Kuhar, M. J, Eds, Springer: Berlin
    • Kreek, M. J. In Handbook of Experimental Pharmacology; Schuster. C. R., Kuhar, M. J., Eds.; Springer: Berlin, 1996; Vol. 118, p 563.
    • (1996) Handbook of Experimental Pharmacology , vol.118 , pp. 563
    • Kreek, M.J.1
  • 3
    • 0033528748 scopus 로고    scopus 로고
    • Acute heroin overdose
    • Sporer, K. A. Acute heroin overdose. Ann. Intern. Med. 1999, 130, 84-90.
    • (1999) Ann. Intern. Med , vol.130 , pp. 84-90
    • Sporer, K.A.1
  • 4
    • 0020038669 scopus 로고
    • Common anionic receptor site hypothesis: Its relevance to the antagonist action of naloxone
    • Kobylecki, R. J.; Carling, R. W.; Lord, J. A. H.; Smith, C. F. C.; Lane, A. C. Common anionic receptor site hypothesis: Its relevance to the antagonist action of naloxone. J. Med. Chem. 1982, 25, 116-120.
    • (1982) J. Med. Chem , vol.25 , pp. 116-120
    • Kobylecki, R.J.1    Carling, R.W.2    Lord, J.A.H.3    Smith, C.F.C.4    Lane, A.C.5
  • 6
    • 0037464482 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of 14-alkoxymorphinans. 18. N-Substituted 14-phenylpropyloxymorphinan-6-ones with unanticipated agonist properties: Extending the scope of common structure- activity relationships
    • Greiner, E.; Spetea, M.; Krassnig, R.; Schuller, F.; Aceto, M. D.; Harris, L. S.; Traynor, J. R.; Woods, J. H.; Coop, A.; Schmidhammer, H. Synthesis and biological evaluation of 14-alkoxymorphinans. 18. N-Substituted 14-phenylpropyloxymorphinan-6-ones with unanticipated agonist properties: Extending the scope of common structure- activity relationships. J. Med. Chem. 2003, 46, 1758-1763.
    • (2003) J. Med. Chem , vol.46 , pp. 1758-1763
    • Greiner, E.1    Spetea, M.2    Krassnig, R.3    Schuller, F.4    Aceto, M.D.5    Harris, L.S.6    Traynor, J.R.7    Woods, J.H.8    Coop, A.9    Schmidhammer, H.10
  • 7
    • 0024567173 scopus 로고
    • Very long-acting narcotic antagonists: The 14β-p-substituted cinnamoylaminomorphinones and their partial mu agonist codeinone relatives
    • Aceto, M. D.; Bowmen, E. R.; May, E. L.; Woods, J. H.; Smith, C. B.; Medzihradsky, F.; Jacobson, A. E. Very long-acting narcotic antagonists: The 14β-p-substituted cinnamoylaminomorphinones and their partial mu agonist codeinone relatives. Arzneim. Forsch. 1989, 39, 570-575.
    • (1989) Arzneim. Forsch , vol.39 , pp. 570-575
    • Aceto, M.D.1    Bowmen, E.R.2    May, E.L.3    Woods, J.H.4    Smith, C.B.5    Medzihradsky, F.6    Jacobson, A.E.7
  • 8
    • 0033838122 scopus 로고    scopus 로고
    • Methcinnamox is a potent, long- lasting and selective antagonist of morphine-mediated antinociception in the mouse: Comparison with clocinnamox, β-FNA and β-chlorn-altrexamine
    • Broadbear, J. H.; Sumpter, T. L.; Burke, T. F.; Husbands, S. M.; Lewis, J. W.; Woods, J. H.; Traynor, J. R. Methcinnamox is a potent, long- lasting and selective antagonist of morphine-mediated antinociception in the mouse: Comparison with clocinnamox, β-FNA and β-chlorn-altrexamine. J. Pharmacol. Exp. Ther. 2000, 294, 933-940.
    • (2000) J. Pharmacol. Exp. Ther , vol.294 , pp. 933-940
    • Broadbear, J.H.1    Sumpter, T.L.2    Burke, T.F.3    Husbands, S.M.4    Lewis, J.W.5    Woods, J.H.6    Traynor, J.R.7
  • 9
    • 33747483001 scopus 로고    scopus 로고
    • Structural determinants of opioid activity in derivatives of 14-aminomorphinones: Effect of substitution in the aromatic ring of cinnamoylaminomor-phinones and codeinones
    • Nieland, N. P. R.; Moynihan, H.; Carrington, S.; Broadbear, J.; Woods, J. H.; Traynor, J. R.; Husbands, S. M.; Lewis, J. W. Structural determinants of opioid activity in derivatives of 14-aminomorphinones: Effect of substitution in the aromatic ring of cinnamoylaminomor-phinones and codeinones. J. Med. Chem. 2006, 49, 5333-5338.
    • (2006) J. Med. Chem , vol.49 , pp. 5333-5338
    • Nieland, N.P.R.1    Moynihan, H.2    Carrington, S.3    Broadbear, J.4    Woods, J.H.5    Traynor, J.R.6    Husbands, S.M.7    Lewis, J.W.8
  • 10
    • 33749249732 scopus 로고    scopus 로고
    • Structural determinants of opioid activity in derivatives of 14- aminomorphinones: Effects of changes to the C14-amino to aryl ring linker chain
    • Rennison, D.; Moynihan, H.; Traynor, J. R.; Lewis, J. W.; Husbands, S. M. Structural determinants of opioid activity in derivatives of 14- aminomorphinones: Effects of changes to the C14-amino to aryl ring linker chain. J. Med. Chem. 2006, 49, 6104-6110.
    • (2006) J. Med. Chem , vol.49 , pp. 6104-6110
    • Rennison, D.1    Moynihan, H.2    Traynor, J.R.3    Lewis, J.W.4    Husbands, S.M.5
  • 11
    • 0038337162 scopus 로고    scopus 로고
    • Novel enzymatic synthesis of 4-o-cinnamoyl quinic and shikimic acid derivatives
    • Armesto, N.; Ferrero, M.; Fernandez, S.; Gotor, V. Novel enzymatic synthesis of 4-o-cinnamoyl quinic and shikimic acid derivatives. J. Org. Chem. 2003, 68, 5784-5787.
    • (2003) J. Org. Chem , vol.68 , pp. 5784-5787
    • Armesto, N.1    Ferrero, M.2    Fernandez, S.3    Gotor, V.4
  • 14
    • 0035964719 scopus 로고    scopus 로고
    • Characterization of opiates, neuroleptics, and synthetic analogs at ORL1 and opioid receptors
    • Zaveri, N.; Polgar, W. E.; Olsen, C. M.; Kelson, A. B.; Grundt, P.; Lewis, J. W.; Toll, L. Characterization of opiates, neuroleptics, and synthetic analogs at ORL1 and opioid receptors. Eur. J. Pharmacol. 2001, 428, 29-36.
    • (2001) Eur. J. Pharmacol , vol.428 , pp. 29-36
    • Zaveri, N.1    Polgar, W.E.2    Olsen, C.M.3    Kelson, A.B.4    Grundt, P.5    Lewis, J.W.6    Toll, L.7
  • 15
    • 0002448256 scopus 로고
    • The interaction of buprenorphine with the opiate receptor
    • Kosterlitz, H. W, Ed, Elsevier: Amsterdam
    • Hambrook, J. M.; Rance, M. J. The interaction of buprenorphine with the opiate receptor. In Opiates and Endogenous Opioid Peptides; Kosterlitz, H. W., Ed.; Elsevier: Amsterdam, 1976; pp 295-301.
    • (1976) Opiates and Endogenous Opioid Peptides , pp. 295-301
    • Hambrook, J.M.1    Rance, M.J.2
  • 16
    • 0028293519 scopus 로고
    • In vivo determination of mu opioid receptor turnover in rhesus monkeys after irreversible blockade with clocinnamox
    • Zernig, G.; Butelman, E. R.; Lewis, J. W.; Walker, E. A.; Woods, J. H. In vivo determination of mu opioid receptor turnover in rhesus monkeys after irreversible blockade with clocinnamox. J. Pharmacol. Exp. Ther. 1994, 269, 57-65.
    • (1994) J. Pharmacol. Exp. Ther , vol.269 , pp. 57-65
    • Zernig, G.1    Butelman, E.R.2    Lewis, J.W.3    Walker, E.A.4    Woods, J.H.5
  • 17
    • 0027367655 scopus 로고
    • 14β-[(p-Nitrocinnamoyl)amino]morphinones, 14β- [p-nitrocinnamoyl)amino]-7,8-dihydromorphinones and their codeino-ne analogues: Synthesis and receptor activity
    • Sebastian, A.; Bidlack, J. M.; Jiang, Q.; Deecher, D.; Teitler, M.; Glick, S. D.; Archer, S. 14β-[(p-Nitrocinnamoyl)amino]morphinones, 14β- [p-nitrocinnamoyl)amino]-7,8-dihydromorphinones and their codeino-ne analogues: Synthesis and receptor activity. J. Med. Chem. 1993, 36, 3154-3160.
    • (1993) J. Med. Chem , vol.36 , pp. 3154-3160
    • Sebastian, A.1    Bidlack, J.M.2    Jiang, Q.3    Deecher, D.4    Teitler, M.5    Glick, S.D.6    Archer, S.7
  • 18
    • 0037674014 scopus 로고    scopus 로고
    • Opioid ligands having delayed long-term antagonist activity: Potential pharmacotherapies for opioid abuse
    • Husbands, S. M.; Lewis, J. W. Opioid ligands having delayed long-term antagonist activity: Potential pharmacotherapies for opioid abuse. Mini-Rev. Med. Chem. 2003, 3, 137-144.
    • (2003) Mini-Rev. Med. Chem , vol.3 , pp. 137-144
    • Husbands, S.M.1    Lewis, J.W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.