Structural determinants of opioid activity in derivatives of 14-aminomorphinones: Effect of substitution in the aromatic ring of cinnamoylaminomorphinones and codeinones

Journal of Medicinal Chemistry

Volumn 49, Issue 17, 2006, Pages 5333-5338

  Nieland, Nick P R ^a   Moynihan, Humphrey A ^a   Carrington, Simon ^a   Broadbear, Jillian ^c   Woods, James H ^c   Traynor, John R ^c   Husbands, Stephen M ^b   Lewis, John W ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b University of Bath   (United Kingdom)

^c UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

14BETA (2' CHLOROCINNAMOYLAMINO) 7,8 DIHYDROMORPHINONE; 14BETA (2' CHLOROCINNAOYLAMINO) 7,8 DIHYDROCODEINONE; 14BETA (2' METHYLCINNAMOYLAMINO) 7,8 DIHYDROCODEINONE; 14BETA (2' METHYLCINNAMOYLAMINO) 7,8 DIHYDROMORPHINONE; AROMATIC COMPOUND; CHLORINE DERIVATIVE; CLOCINNAMOX; CODEINE; CYCLOPROPANE DERIVATIVE; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; ENKEPHALIN[2,5 DEXTRO PENICILLAMINE]; LIGAND; METHOCLOCINNAMOX; METHYL GROUP; MORPHINE; MORPHINONE; MU OPIATE RECEPTOR; N CYCLOPROPYLMETHYL 14BETA (2' CHLOROCINNAMOYLAMINO) 7,8 DIHYDRONORCODEINONE; N CYCLOPROPYLMETHYL 14BETA (2' METHYLCINNAMOYLAMINO) 7,8 DIHYDRONORCODEINONE; N CYCLOPROPYLMETHYL 14BETA (2' NITROCINNAMOYLAMINO) 7,8 DIHYDRONORMORPHINONE; N METHYL N [7 (1 PYRROLIDINYL) 1 OXASPIRO[4.5]DEC 8 YL]BENZENEACETAMIDE; NALTREXONE; NITRO DERIVATIVE; OPIATE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINOCICEPTION; ARTICLE; CHO CELL; CONTROLLED STUDY; DRUG EFFICACY; DRUG POTENCY; DRUG RECEPTOR BINDING; LIGAND BINDING; NONHUMAN; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; TAIL FLICK TEST;

CINNAMATES; CODEINE; DRUG DESIGN; LIGANDS; MOLECULAR STRUCTURE; MORPHINE DERIVATIVES; RECEPTORS, OPIOID, MU; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33747483001     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0604777     Document Type: Article

References (29)

1. Portoghese, P. S.; Sultana, M.; Takemori, A. E. Naltrindole, a highly selective and potent non-peptide δ opioid antagonist. Eur. J. Pharmacol. 1988, 146, 185-186.
2. Portoghese, P. S.; Lipkowski, A. W.; Takemori, A. E. Bimorphinans as highly selective, potent κ-opioid receptor antagonists. J. Med. Chem. 1987, 30, 238.
3. Jones, R. M.; Hjorth, S. A.; Schwartz, T. W.; Portoghese, P. S. Mutational evidence for a common κ antagonist binding pocket in the wild-type κ and mutant μ [K303E] opioid receptors. J. Med. Chem. 1998, 41, 4911-4914.
4. Greiner, E.; Spetea, M.; Krassnig, R.; Schullner, F.; Aceto, M.; 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.
5. 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.
6. Comer, S. D.; Burke, T. F.; Lewis, J. W.; Woods, J. H. Clocinnamox: a novel, systemically active irreversible opioid antagonist. J. Pharmacol. Exp. Ther. 1992, 262, 1051-1056.
7. 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-chlornaltrexamine. J. Pharmacol Exp. Ther. 2000, 294, 933-940.
8. Woods, J. H.; Lewis, J. W.; Winger, G.; Butelman, E.; Broadbear, J.; Zernig, G. Methoclocinnamox: a μ partial agonist with pharmacotherapeutic potential for heroin abuse. NIDA Res. Monogr. 1995, 147, 195-219.
9. 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./Drug Res. 1989, 39, 570-575.
10. 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 codeinone analogues: synthesis and receptor activity. J. Med. Chem. 1993, 36, 3154-3160.
11. Kirby, G.; McLean, D. An efficient synthesis of 14β-aminocodeinone from thebaine. J. Chem. Soc., Perkin Trans, 1 1985, 1443-1445.
12. Rice, K. C. A rapid, high-yield conversion of codeine to morphine. J. Med. Chem. 1977, 20, 164-165.
13. Nieland, N. Investigations of derivatives of 14β-amino-7,8- dihydromorphinone. Ph.D. Thesis, University of Bristol, U.K., 1998.
14. 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.
15. Husbands, S. M.; Sadd, J.; Broadbear, J. H.; Woods, J. H.; Martin, J.; Traynor, J. R.; Aceto, M. D.; Bowman, E. R.; Harris, L. S.; Lewis, J. W. 3-Alkyl ethers of clocinnamox: Delayed long-term μ-antagonists with variable μ efficacy. J. Med. Chem. 1998, 41, 3493-3498.
16. Traynor, J. R.; Nahorski, S. R. Modulation by mu-opioid agonists of guanosine-5′-O-(3-[S-35]thio)triphosphate binding to membranes from human neuroblastoma SH-SY5Y cells. Mol. Pharmacol. 1995, 47, 848-854.
17. Toll, L.; Berzetei-Gurske, I. P.; Polgar, W. E.; Brandt, S. R.; Adapa, I. D.; Rodriguez, L.; Schwartz, R. W.; Haggart, D.; O'Brien, A.; White, A.; Kennedy, J. M.; Craymer, K.; Farrington, L.; Auh, J. S. Standard binding and functional assays related to (NIDA) Medications Development Division testing for potential cocaine and narcotic treatment programs. NIDA Res. Monogr. 1998, 178, 440-466.
18. Aceto, M. D.; Bowman, E. R.; Harris, L. S.; May, E. L. Dependence studies of new compounds in the rhesus monkey, rat and mouse. 1989. NIDA Res. Monogr. 1990, 95, 578-631. 4c is designated NIH10545. 8b is designated NIH10594, and 8c is designated 10544.
19. Aceto, M. D.; Harris, L. S.; Bowman, E. R. Etorphines: μ-opioid receptor-selective antinociception and low physical dependence capacity. Eur. J. Pharmacol. 1997, 338, 215-223.
20. Tyers, M. B. A classification of opiate receptors that mediate antinociception in animals. Br. J. Pharmacol. 1980, 69, 503-512.
21. Aceto, M. D.; Harris, L. S.; May, E. L. Dependence studies of new compounds in the rhesus monkey, rat and mouse. 1983. NIDA Res. Monogr. 1984, 49, 368-420. Compound 9 is designated NIH9917.
22. Aceto, M. D.; Bowman, E. R.; Harris, L. S.; May, E. L. Dependence studies of new compounds in the rhesus monkey, rat and mouse. 1990. NIDA Res. Monogr. 1991, 105, 640-681. 6a is designated NIH10630.
23. Aceto, M. D.; Bowman, E. R.; Harris, L. S.; May, E. L. Dependence studies of new compounds in the rhesus monkey, rat and mouse. 1997. NIDA Res. Monogr. 1998, 178, 363-407.
24. Aceto, M. D.; Bowman, E. R.; Harris, L. S.; May, E. L. Dependence studies of new compounds in the rhesus monkey, rat and mouse. 2003. NIDA Res. Monogr. 2004, 184, 170-204. 5f is designated NIH11122, and 7b is designated NIH11124.
25. McLaughlin, J. P.; Hill, K. P.; Jiang, Q.; Sebastian, A.; Archer, S.; Bidlack, J. M. Nitrocinnamoyl and chlorocinnamoyl derivatives of dihydrocodeinone: in vivo and in vitro characterization of μ-selective agonist and antagonist activity. J. Pharmacol. Exp. Ther. 1999, 289, 304-311.
26. Craig, P. N. Physical chemical factors in drug design. In Burger's Medicinal Chemistry, 4th ed.; Wolff, M. E., Ed.; John Wiley and Sons: New York, 1980; Part 1.
27. Husbands, S. M.; Lewis, J. W. Structural determinants of efficacy for κ-opioid receptors in the orvinol series: 7,7-spiro analogues of buprenorphine. J. Med. Chem. 2000, 43, 139-141.
28. Husbands S. M.; Neilan, C.; Broadbear, J.; Grundt, P.; Breeden, S.; Aceto, M.; Woods, J. H.; Lewis, J. W.; Traynor, J. R. BU74, a complex oripavine derivative with potent kappa opioid receptor agonism and delayed opioid antagonism. Eur. J. Pharmacol. 2005, 509, 117-125.
29. Rennison, D.; Moynihan, H. A.; 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. Manuscript submitted.