Novel cleavage reaction of the C16-N17 bond in naltrexone derivatives

Tetrahedron Letters

Volumn 49, Issue 44, 2008, Pages 6293-6296

  Fujii, Hideaki ^a   Imaide, Satomi ^a   Watanabe, Akio ^a   Nemoto, Toru ^a   Nagase, Hiroshi ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

Chloroformate; Dealkylation; Morphinan; Stereoelectronic effect

Indexed keywords

CATION; NALTREXONE DERIVATIVE; TERTIARY AMINE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DEALKYLATION; POLARIZATION; REACTION ANALYSIS;

EID: 51549119031     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.08.037     Document Type: Article

References (24)

1. Casy A.F., and Parfitt R.T. Opioid Analgesics (1986), Plenum Press, New York
2. Hagemen H.A. Org. React. 7 (1953) 198
3. von Braun J. Ber. 47 (1914) 2312
4. Bentley K.W., and Hardy D.G. J. Am. Chem. Soc. 89 (1967) 3281
5. Cooley J.H., and Evain E.J. Synthesis (1989) 1
6. Montzka T.A., Matiskella J.D., and Partyka R.A. Tetrahedron Lett. 15 (1974) 1325
7. Olofson A.R., Schnur R.C., Bunes L., and Pepe J.P. Tetrahedron Lett. 18 (1977) 1567
8. Olofson R.A., Martz J.T., Senet J.P., Piteau M., and Malfroot T. J. Org. Chem. 49 (1984) 2081
9. Although morphine is a classical μ opioid receptor agonist, its intrinsic activity is known to be lower than that of a representative μ opioid receptor full agonist, DAMGO. Moreover, it was recently reported that morphine was a partial agonist for opioid μ receptor in some pharmacological assays. See the following references:. Selley D.E., Sim L.J., Xiao R., Liu Q., and Childers S.R. Mol. Pharmacol. 51 (1997) 87
10. Brown G.P., Yang K., Ouerfelli O., Standifer K.M., Byrd D., and Pasternak G.W. J. Pharmacol. Exp. Ther. 282 (1997) 1291
11. Traynor J.R., Clark M.J., and Remmers A.E. J. Pharmacol. Exp. Ther. 300 (2002) 157
12. Schulz S., Mayer D., Pfeiffer M., Stumm R., Koch T., and Höllt V. EMBO J. 23 (2004) 3282
13. Johnson E.A., Oldfield S., Braksator E., Gonzalez-Cuello A., Couch D., Hall K.J., Mundell S.J., Bailey C.P., Kelly E., and Henderson G. Mol. Pharmacol. 70 (2006) 676
14. +: 462.1683; found 462.1675.
15. +: 388.1760; found 388.1809.
16. Gould E.S. Mechanism and Structure in Organic Chemistry (1959), Henry Holt and Company, New York 561-617
17. Richey, H. G., Jr. In Carbonium Ions; Olah, G. A., Schleyer, P. R., Eds.; John Wiley & Sons: Canada, 1972; Vol. III. pp 1201-1294.
18. Lowry T.H., and Richardson K.S. Mechanism and Theory in Organic Chemistry. 3rd ed. (1987), Harper & Row Publishers, New York pp 425-515
19. Olah G.A., Prakash Reddy V., and Surya Prakash G.K. Chem. Rev. 92 (1992) 69
20. Nagase, H.; Yamamoto, N.; Nemoto, T.; Yoza, K.; Kamiya, K.; Hirono, S.; Momen, S.; Izumimoto, N.; Hasebe, K.; Mochizuki, H.; Fujii, H. J. Org. Chem., in press.
21. Fujii, H.; Osa, Y.; Ishihara, M.; Hanamura, S.; Nemoto, T.; Nakajima, M.; Hasebe, K.; Mochizuki, H.; Nagase, H. Bioorg. Med. Chem. Lett., in press. doi:10.1016/j.bmcl.2008.08.019.
22. Kapnang H., and Charles G. Tetrahedron Lett. 24 (1983) 3233
23. Mayr H., and Olah G.A. J. Am. Chem. Soc. 99 (1977) 510
24. van Alem K., Lodder G., and Zuilhof H. J. Phys. Chem. A 106 (2002) 10681