Synthesis of novel twin drug consisting of 8-oxaendoethanotetrahydromorphides with a 1,4-dioxane spacer and its pharmacological activities: μ, κ, and putative ε opioid receptor antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 2, 2009, Pages 438-441

  Fujii, Hideaki ^a   Watanabe, Akio ^a   Nemoto, Toru ^a   Narita, Minoru ^b   Miyoshi, Kan ^b   Nakamura, Atsushi ^b   Suzuki, Tsutomu ^b   Nagase, Hiroshi ^a  

^a KITASATO UNIVERSITY   (Japan)

^b HOSHI UNIVERSITY   (Japan)

Author keywords

Antagonist; Monomer; Opioid; Twin drug

Indexed keywords

8 OXAENDOETHANOTETRAHYDROMORPHIDE; DIOXANE; EPSILON OPIATE RECEPTOR ANTAGONIST; G PROTEIN COUPLED RECEPTOR; KAPPA OPIATE RECEPTOR ANTAGONIST; MU OPIATE RECEPTOR ANTAGONIST; NALTREXONE DERIVATIVE; NS 29; TAN 1014; TAN 821; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DEMETHYLATION; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HOT PLATE TEST; LIPOPHILICITY; MOUSE; NONHUMAN; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; TAIL FLICK TEST; X RAY CRYSTALLOGRAPHY;

ANIMALS; BRAIN; CRYSTALLOGRAPHY, X-RAY; DIOXANES; MICE; MODELS, MOLECULAR; MORPHINE DERIVATIVES; NALTREXONE; NARCOTIC ANTAGONISTS; RECEPTORS, OPIOID; RECEPTORS, OPIOID, KAPPA; RECEPTORS, OPIOID, MU;

EID: 57749104689     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.11.050     Document Type: Article

References (21)

1. Dhawan B.N., Cesselin F., Raghubir T., Reisine T., Bradley P.B., Portoghese P.S., and Hamon M. Pharmacol. Rev. 48 (1996) 567 (and references cited therein)
2. Fujii H., and Nagase H. Curr. Med. Chem. 13 (2006) 1109 (and references cited therein)
3. Rios C.D., Jordan B.A., Gomes I., and Devi L.A. Pharmacol. Ther. 92 (2001) 71
4. Angers S., Salahpour A., and Bouvier M. Annu. Rev. Pharmacol. Toxicol. 42 (2002) 409
5. Prinster S.C., Hague C., and Hall R.A. Pharmacol. Rev. 57 (2005) 289
6. Levac B.A.R., O'Dowd B.F., and George S.R. Curr. Opin. Pharmacol. 2 (2002) 76
7. 35S]GTPγS binding assay using the preparations obtained from triple opioid receptor knockout mice. They described that the ε receptor may result from opioid receptor dimerization or from heterodimerization of an opioid receptor with another partner. Contet C., Matifas A., Kieffer B.L. Eur. J. Pharmacol. 492 (2004) 131
8. Fujii H., Narita M., Mizoguchi H., Murachi M., Tanaka T., Kawai K., Tseng L.F., and Nagase H. Bioorg. Med. Chem. 12 (2004) 4133
9. Fujii H., Narita M., Mizoguchi H., Hirokawa J., Kawai K., Tanaka T., Tseng L.F., and Nagase H. Bioorg. Med. Chem. Lett. 14 (2004) 4241
10. Watanabe A., Kai T., and Nagase H. Org. Lett. 8 (2006) 523
11. Contreras J.-M., and Bourguignon J.-J. The Practice of Medicinal Chemistry. 2nd ed. In: Wermth C.G. (Ed) (2003), Academic Press, London 251-273
12. Portoghese P.S., Nagase H., Lipkowski A.W., Larson D.L., and Takemori A.E. J. Med. Chem. 31 (1988) 836
13. Stoddart J.F. Comprehensive Organic Chemistry Vol. 1 (1979), Springer, Berlin pp 1002-1003
14. Crystallographic data of compound 8 have been deposited with the Cambridge Crystallographic Data Center as supplementary Publication No. CCDC 705154. These data can be obtained free of charge from the Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif.
15. Nagase H., Watanabe A., Nemoto T., Yamamoto N., Osa Y., Sato N., Yoza K., and Kai T. Tetrahedron Lett. 48 (2007) 2547
16. 35S]GTPγS binding assay. Mizoguch H., Narita M., Nagase H., and Tseng L.F. Life Sci. 67 (2000) 2733
17. Portoghese P.S. Trends Pharmacol. Sci. 10 (1989) 230
18. Portoghese P.S., Sultana M., Nagase H., and Takemori A.E. J. Med. Chem. 31 (1998) 281
19. Nagase H., Kawai K., Hayakawa J., Wakita H., Mizusuna A., Matsuura H., Tajima C., Takezawa Y., and Endo T. Chem. Pharm. Bull. 46 (1998) 1695
20. Kawai K., Hayakawa J., Miyamoto T., Imamura Y., Yamane S., Wakita H., Fujii H., Kawamura K., Matsuura H., Izumimoto N., Kobayashi R., Endo T., and Nagase H. Bioorg. Med. Chem. 16 (2008) 9188
21. Nogrady T. In: Nogrady T. (Ed). Medicinal Chemistry, A Biochemical Approach (1985), Springer, Berlin pp 68-69