A novel solid-phase reductive alkylation route to acridine and dansyl polyamine conjugates

(Note: The full text of this document is currently only available in the PDF Version )

Simon Carrington, Ian S. Blagbrough, Jacques Renault, Sophie Tomasi, Jean-Charles Corbel and Philippe Uriac


Abstract

Solid-phase organic synthesis (SPOS) routes to target unsymmetrical polyamines and their acridinyl and dansyl conjugates have been developed based upon borane–pyridine complex (BAP) mediated reductive alkylation, azide reduction with triphenylphosphine, and the use of pent-4-enoyl (Pnt) as an orthogonal amine protecting group.


References

  1. I. S. Blagbrough, S. Carrington and A. J. Geall, Pharm. Sci., 1997, 3, 223 CAS and references cited therein..
  2. S. Carrington, A. H. Fairlamb and I. S. Blagbrough, Chem. Commun., 1998, 2335 RSC and references cited therein..
  3. I. S. Blagbrough, S. Taylor, M. L. Carpenter, V. Novoselskiy, T. Shamma and I. S. Haworth, Chem. Commun., 1998, 929 RSC and references cited therein..
  4. J. Chao, N. Seiler, J. Renault, K. Kashiwagi, T. Masuko, K. Igarashi and K. Williams, Mol. Pharmacol., 1997, 51, 861 Search PubMed.
  5. P. Durand, P. Richard and P. Renaut, J. Org. Chem., 1998, 63, 9723 CrossRef CAS and references cited therein..
  6. M. C. O'Sullivan, Q. Zhou, Z. Li, T. B. Durham, D. Rattendi, S. Lane and C. J. Bacchi, Bioorg. Med. Chem., 1997, 5, 2145 CrossRef CAS.
  7. S. K. Choi, K. Nakanishi and P. N. R. Usherwood, Tetrahedron, 1993, 49, 5777 CrossRef CAS; D. W. Huang, H. Jiang, K. Nakanishi and P. N. R. Usherwood, Tetrahedron, 1997, 53, 12391 CrossRef CAS.
  8. B. T. Golding, A. Mitchinson, W. Clegg, M. R. J. Elsegood and R. J. Griffin, J. Chem. Soc., Perkin Trans. 1, 1999, 349 RSC.
  9. I. R. Marsh, H. Smith and M. Bradley, Chem. Commun., 1996, 941 RSC; I. R. Marsh, H. K. Smith, C. LeBlanc and M. Bradley, Mol. Diversity, 1997, 2, 165 Search PubMed; I. R. Marsh and M. Bradley, Tetrahedron, 1997, 53, 17317 CrossRef CAS; P. Page, S. Burrage, L. Baldock and M. Bradley, Bioorg. Med. Chem. Lett., 1998, 8, 1751 CrossRef CAS.
  10. A. Nefzi, C. Dooley, J. M. Ostresh and R. A. Houghten, Bioorg. Med. Chem. Lett., 1998, 8, 2273 CrossRef CAS; A. Nefzi, J. M. Ostresh and R. A. Houghten, Tetrahedron, 1999, 55, 335 CrossRef CAS.
  11. B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415 CrossRef CAS; I. A. Nash, B. W. Bycroft and W. C. Chan, Tetrahedron Lett., 1996, 37, 2625 CrossRef CAS.
  12. G. Byk, M. Frederic and D. Scherman, Tetrahedron Lett., 1997, 38, 3219 CrossRef CAS; G. Byk, C. Dubertret, V. Escriou, M. Frederic, G. Jaslin, R. Rangara, B. Pitard, J. Crouzet, P. Wils, B. Schwartz and D. Scherman, J. Med. Chem., 1998, 41, 224 CrossRef.
  13. S. Tomasi, M. Le Roch, J. Renault, J.-C. Corbel, P. Uriac, B. Carboni, D. Moncoq, B. Martin and J.-G. Delcros, Bioorg. Med. Chem. Lett., 1998, 8, 635 CrossRef CAS.
  14. B. Carboni, M. Vaultier and R. Carrie, Tetrahedron, 1987, 43, 1799 CrossRef CAS.
  15. R. Madsen, C. Roberts and B. Fraser-Reid, J. Org. Chem., 1995, 60, 7920 CrossRef CAS.
  16. D. M. Dixit and C. C. Leznoff, J. Chem. Soc., Chem. Commun., 1977, 798 RSC.
  17. G. C. Look, C. P. Holmes, J. P. Chinn and M. A. Gallop, J. Org. Chem., 1994, 59, 7588 CrossRef CAS.
  18. N. M. Kahn, V. Arumugam and S. Balasubramanian, Tetrahedron Lett., 1996, 37, 4819 CrossRef; E. E. Swayze, Tetrahedron Lett., 1997, 38, 8465 and 8643 CrossRef.
  19. B. Carboni, A. Benalil and M. Vaultier, J. Org. Chem., 1993, 58, 3736 CrossRef CAS.
  20. R. P. Iyer, D. Yu, N. H. Ho, T. Devlin and S. Agrawal, J. Org. Chem., 1995, 60, 8132 CrossRef CAS; I. Habus, J. Xie, R. P. Iyer, W.-Q. Zhou, L. X. Shen and S. Agrawal, Bioconjugate Chem., 1998, 9, 283 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.