The 4-azidobenzyloxycarbonyl function; application as a novel protecting group and potential prodrug modification for amines

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 11, 1996, Pages 1205-1211

  Griffin, Roger J ^a   Evers, Elaine ^b   Davison, Richard ^a   Gibson, Ashleigh E ^a   Layton, Deborah ^b   Irwin, William J ^b  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

^b ASTON UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002934074     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960001205     Document Type: Article

References (35)

1. (a) S. Patai, The Chemistry of the Azido Group, Wiley, London, 1971;
2. (b) E. F. V. Scriven, Azides and Nitrenes; Reactivity and Utility, Academic Press, London, 1984;
3. (c) E. F. V. Scriven and K. Turnbull, Chem. Rev., 1988, 88, 297.
4. R. J. Griffin, Prog. Med. Chem., 1994, 31, 121.
5. P. A. S. Smith, in Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds, ed. P. A. S. Smith, Benjamin/Cummings, Massachusetts, 1983, pp. 263-293.
6. E. M. Cretton and J. P. Sommadossi, Drug Metabolism and Disposition, 1993, 21, 946.
7. M. F. G. Stevens, R. J. Griffin and S. K. Wong, Anti-cancer Drug Des., 1987, 2, 311.
8. F. Kamali, A. Gescher and J. A. Slack, Xenobiotica, 1988, 18, 1157.
9. D. Nicholls, A. Gescher and R. J. Griffin, Xenobiotica, 1991, 21, 935.
10. (a) I. L. Cartwright, D. W. Hutchinson and V. W. Armstrong, Nucleic Acids Res., 1976, 3, 2331;
11. (b) H. Bayley, J. R. Standring and J. R. Knowles, Tetrahedron Lett., 1978, 39, 3633.
12. J. V. Staros, H. Bayley, D. N. Standring and J. R. Knowles, Biochem. Biophys. Res. Commun., 1978, 80, 568.
13. A. L. Handlon and N. J. Oppenheimer, Pharm. Res., 1988, 5, 297.
14. N. D. Baker, R. J. Griffin and W. J. Irwin, Int. J. Pharm., 1990, 65, 115.
15. A. Naik, W. J. Irwin and R. J. Griffin, Int. J. Pharm., 1993, 89, 51, 65.
16. A. Naik, W. J. Irwin and R. J. Griffin, Int. J. Pharm., 1993, 90, 129.
17. R. H. Guy, N. Higo, A. Naik, D. Bommannan, V. Ramanathan, R. Griffin, W. J. Irwin and R. O. Potts, in Mechanism and Enhancement of Skin Penetration in vivo, Prediction of Percutaneous Penetration: Methods, Measurements, Modelling, eds. R. C. Scott, R. H. Guy, J. Hadgraft and H. E. Boddé, 1991, pp. 1-12.
18. P. L. Carl, P. K. Chakravarty and J. A. Katzenellenbogen, J. Med. Chem., 1981, 24, 479.
19. C. Hansch and A. J. Leo, Substituent Constants for Correlation Analysis in Chemistry and Biology, Wiley, New York, 1979.
20. A. Mitchinson, B. T. Golding, R. J. Griffin and M. C. O'Sullivan, J. Chem. Soc., Chem. Commun., 1994, 2613.
21. W. Thomson, D. Nicholls, W. J. Irwin, J. S. Al-Mushadani, S. Freeman, A. Karpas, J. Petrik, N. Mahmood and A. J. Hay, J. Chem. Soc., Perkin Trans. 1, 1993, 1239.
22. K. Fukase, M. Hashida and S. Kusumoto, Tetrahedron Lett., 1991, 32, 3557.
23. B. Loubinoux and P. Gerardin, Tetrahedron Lett., 1991, 32, 35.
24. A-M. Robinson, E. L. Evers, R. J. Griffin and W. J. Irwin, J. Pharm. Pharmacol., 1988, 40, 61P.
25. T. Mukaiyama and T. Akiba, Bull. Chem. Soc. Jpn, 1960, 33, 1707.
26. H. A. Staab, Angew. Chem., Int. Ed. Engl., 1962, 1, 351.
27. G. W. Anderson and A. C. McGregor, J. Am. Chem. Soc., 1957, 79, 6181;
28. R. A. Boissonnas, Adv. Org. Chem., 1963, 3, 159.
29. D. R. Kelly and M. Gingell, Chem. Ind. (London), 1991, 23, 888.
30. R. L. Letsinger and K. K. Ogilvie, J. Org. Chem., 1967, 32, 296.
31. E. D. Laganis and B. L. Chenard, Tetrahedron Lett., 1984, 25, 5831.
32. N. D. Baker, R. J. Griffin, W. J. Irwin and J. A. Slack, Int. J. Pharm., 1989, 52, 231.
33. W. L. Zahler and W. W. Cleland, J. Biol. Chem., 1968, 243, 716.
34. W. J. Irwin, Kinetics of Drug Decomposition: BASIC Computer Solutions, Elsevier, Amsterdam, 1990.
35. N. C. Bergstrom and A. E. Martell, J. Am. Chem. Soc., 1945, 67, 494.