Discrimination of spermidine amino functions by a new protecting group strategy; application to the synthesis of guanidinylated polyamines, including hirudonine

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 22, 1994, Pages 2613-2614

  Mitchinson, Andrew ^a   Golding, Bernard T ^a   Griffin, Roger J ^a   O'Sullivan, Mary C ^a  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 AZIDOBENZYLOXYCARBONYL; AGMATINE; AMINE; CARBONYL DERIVATIVE; GUANIDINE DERIVATIVE; HIRUDIN DERIVATIVE; HIRUDONINE; N NITROGUANIDINYL; POLYAMINE; PUTRESCINE; SPERMIDINE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; PRECURSOR; STRUCTURE ACTIVITY RELATION;

EID: 0028006870     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39940002613     Document Type: Article

References (25)

1. A. E. Pegg, Cancer Res., 1988, 48, 759.
2. C. W. Porter and J. R. Sufrin, Anticancer Res., 1986, 6, 525.
3. N. Seiler and F. Dezeure, Int. J. Biochem., 1990, 22, 211.
4. D. M. L. Morgan, Biochem. J., 1992, 286, 413.
5. M. C. O’Sullivan, B. T. Golding, L. L. Smith and I. Wyatt, Biochem. Pharmacol., 1991, 41, 1839.
6. C. W. Porter, P. F. Cavanaugh, N. Stolowich, B. Ganis, E. Kelly and R. J. Bergeron, Cancer Res., 1985, 45, 2050.
7. W. D. W. Heston, K. A. Watanabe, K. W. Pankiewicz and D. F. Covey, Biochem. Pharmacol., 1987, 36, 1849.
8. J. L. Holley, A. Mather, R. T. Wheelhouse, P. M. Cullis, J. A. Hartley, J. P. Bingham and G. M. Cohen, Cancer Res., 1992, 52, 4190.
9. G. M. Cohen, P. M. Cullis, J. A. Hartley, A. Mather, M. C. R. Symons and R. T. Wheelhouse, J. Chem. Soc., Chem. Commun., 1992, 298.
10. B. T. Golding, I. K. Nassereddin and M. C. O’Sullivan, Biochem. Soc. Trans., 1990, 18, 1087.
11. K. W. Hart, A. R. Clarke, D. B. Wigley, A. D. B. Waldman, W. N. Chia, D. A. Barstow, T. Atkinson, J. B. Jones and J. J. Holbrook, Biochim. Biophys. Acta, 1987, 914, 294.
12. D. B. Wigley, A. Lyall, K. W. Hart and J. J. Holbrook, Biochem. Biophys. Res. Commun., 1987, 149, 927.
13. U. Regenass, G. Caravatti, H. Mett, J. Stanek, P. Schneider, M. Müller, A. Matter, P. Vertino and C. W. Porter, Cancer Res., 1992, 52, 4712.
14. B.T. Golding, R.J. Griffin, A. Mitchinson and M.C. O’Sullivan, Biochem. Soc. Trans., 1994, A brief account of these results was given at the 651st meeting of the Biochemical Society, Lancaster, UK, July 1994 (see, 223915)
15. Y. Robin, N. van Thoai and L.-A. Pradel, Biochim. Biophys. Acta, 1957, 24, 381.
16. A. F. S. A. Habeeb, Biochim. Biophys. Acta, 1964, 93, 533.
17. J. Boukouvalas, B. T. Golding, R. W. McCabe and P. K. Slaich, Angew. Chem. Suppl., 1983, 860.
18. W. B. Lawson, M. D. Leafer, A. Tewes and G. J. S. Rao, Z. Physiol. Chem., 1968, 349, 251.
19. S.-I. Murahashi, T. Naota and E. Saito, J. Am. Chem. Soc., 1986, 108, 7846.
20. Y. Nagao, K. Seno, T. Miyasaka and E. Fujita, Chem. Lett., 1980, 159.
21. S.-I. Murahashi, T. Naota and N. Nakajima, Chem. Lett., 1987, 879.
22. A. Robinson, E. L. Evers, R. J. Griffin and W. J. Irwin, J. Pharm. Pharmacol., 1988, 40, 61.
23. R.J. Griffin, E.L. Evers, R. Davison, D. Layton and W.J. Irwin, J. Chem. Soc., Perkin Trans. 1, manuscript to be submitted to
24. J. V. Staros, H. Bayley, D. N. Standring and J. R. Knowles, Biochem. Biophys. Res. Commun., 1978, 80, 568.
25. Y. Robin and N. V. Thoai, C. R. Séances Acad. Sci., 1961, 252, 1224.