Structural determinants of efficacy for κ opioid receptors in the orvinol series: 7,7-Spiro analogues of buprenorphine [1]

Journal of Medicinal Chemistry

Volumn 43, Issue 2, 2000, Pages 139-141

  Husbands, Stephen M ^a   Lewis, John W ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BUPRENORPHINE; KAPPA OPIATE RECEPTOR;

ANIMAL CELL; CHO CELL; CONTROLLED STUDY; DRUG EFFICACY; DRUG MECHANISM; DRUG RECEPTOR BINDING; DRUG STRUCTURE; LETTER; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANALGESICS, OPIOID; ANIMALS; BUPRENORPHINE; CHO CELLS; CRICETINAE; MOLECULAR STRUCTURE; RECEPTORS, OPIOID, KAPPA;

EID: 0034719481     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm991165p     Document Type: Letter

References (12)

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3. Coop, A.; Lewis, J. W.; Traynor, J. R. Guo, L. Ring Constrained Analogues of Buprenorphine. NIDA Res. Monogr. 1995, 153, 128.
4. Hutchins, C. W.; Rapoport, H. Analgesics of the Orvinol Type. 19-Deoxy and 6,20-Epoxy Derivatives. J. Med. Chem. 1984, 27, 521-527.
5. Coop, A.; Grivas, K.; Husbands, S. M.; Lewis, J. W.; Porter, J. Ring Constrained Analogues of the Thevinones; Diels Alder Reactions of Thebaines with 1-Indenone and Methylene Cycloalkanones. Tetrahedron Lett. 1995, 36, 1689-1692.
6. Coop, A.; Grivas, K.; Husbands, S. M.; Lewis, J. W. Methylation of the Enolates of Thevinone and some Analogues. Tetrahedron 1995, 51, 9681-9698.
7. NOE studies were performed on a JEOL JNM-GX FT 400 spectrometer. For 10b, irradiation of the C20-proton resulted in enhancement of the 8a-proton.
8. 35S]GTPgammaS binding to membranes from human neuroblastoma SH-SY5Y cells by μ-opioids. Mol. Pharmacol. 1995, 47, 848-854.
9. Magnan, J.; Paterson, S. J.; Tavani, A.; Kosterlitz, H. W. The Binding Spectrum of Narcotic Analgesic Drugs with Different Agonist and Antagonist Properties. Naunyn-Schmiedeberg's Arch. Pharmacol. 1982, 379, 197-205.
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11. Husbands, S. M.; Lewis, J. W. Morphinan Cyclic Imines and Pyrrolidines Containing a Constrained Phenyl Group: High Affinity Opioid Agonists. Bioorg. Med. Chem. Lett. 1995, 5, 2969-2974.
12. PC Spartan Pro utilizing the PM3 semiempirical molecular orbital model. Wave function Inc., California.