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

Chemical Communications

Volumn , Issue 14, 1999, Pages 1341-1342

  Carrington, Simon ^a   Renault, Jacques ^b   Tomasi, Sophie ^b   Corbel, Jean Charles ^b   Uriac, Philippe ^b   Blagbrough, Ian S ^a  

^a University of Bath ^*  (United Kingdom)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE; AZIDE; BORANE DERIVATIVE; DANSYL CHLORIDE; POLYAMINE; PYRIDINE;

ALKYLATION; ARTICLE; CONJUGATE; REDUCTION;

EID: 0033591941     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a904023d     Document Type: Article

References (29)

1. I. S. Blagbrough, S. Carrington and A. J. Geall, Pharm. Sci., 1997, 3, 223 and references cited therein.
2. S. Carrington, A. H. Fairlamb and I. S. Blagbrough, Chem. Commun., 1998, 2335 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 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.
5. P. Durand, P. Richard and P. Renaut, J. Org. Chem., 1998, 63, 9723 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.
7. S. K. Choi, K. Nakanishi and P. N. R. Usherwood, Tetrahedron, 1993, 49, 5777; D. W. Huang, H. Jiang, K. Nakanishi and P. N. R. Usherwood, Tetrahedron, 1997, 53, 12391.
8. S. K. Choi, K. Nakanishi and P. N. R. Usherwood, Tetrahedron, 1993, 49, 5777; D. W. Huang, H. Jiang, K. Nakanishi and P. N. R. Usherwood, Tetrahedron, 1997, 53, 12391.
9. B. T. Golding, A. Mitchinson, W. Clegg, M. R. J. Elsegood and R. J. Griffin, J. Chem. Soc., Perkin Trans. 1, 1999, 349.
10. I. R. Marsh, H. Smith and M. Bradley, Chem. Commun., 1996, 941; I. R. Marsh, H. K. Smith, C. LeBlanc and M. Bradley, Mol. Diversity, 1997, 2, 165; I. R. Marsh and M. Bradley, Tetrahedron, 1997, 53, 17317; P. Page, S. Burrage, L. Baldock and M. Bradley, Bioorg. Med. Chem. Lett., 1998, 8, 1751.
11. I. R. Marsh, H. Smith and M. Bradley, Chem. Commun., 1996, 941; I. R. Marsh, H. K. Smith, C. LeBlanc and M. Bradley, Mol. Diversity, 1997, 2, 165; I. R. Marsh and M. Bradley, Tetrahedron, 1997, 53, 17317; P. Page, S. Burrage, L. Baldock and M. Bradley, Bioorg. Med. Chem. Lett., 1998, 8, 1751.
12. I. R. Marsh, H. Smith and M. Bradley, Chem. Commun., 1996, 941; I. R. Marsh, H. K. Smith, C. LeBlanc and M. Bradley, Mol. Diversity, 1997, 2, 165; I. R. Marsh and M. Bradley, Tetrahedron, 1997, 53, 17317; P. Page, S. Burrage, L. Baldock and M. Bradley, Bioorg. Med. Chem. Lett., 1998, 8, 1751.
13. I. R. Marsh, H. Smith and M. Bradley, Chem. Commun., 1996, 941; I. R. Marsh, H. K. Smith, C. LeBlanc and M. Bradley, Mol. Diversity, 1997, 2, 165; I. R. Marsh and M. Bradley, Tetrahedron, 1997, 53, 17317; P. Page, S. Burrage, L. Baldock and M. Bradley, Bioorg. Med. Chem. Lett., 1998, 8, 1751.
14. A. Nefzi, C. Dooley, J. M. Ostresh and R. A. Houghten, Bioorg. Med. Chem. Lett., 1998, 8, 2273; A. Nefzi, J. M. Ostresh and R. A. Houghten, Tetrahedron, 1999, 55, 335.
15. A. Nefzi, C. Dooley, J. M. Ostresh and R. A. Houghten, Bioorg. Med. Chem. Lett., 1998, 8, 2273; A. Nefzi, J. M. Ostresh and R. A. Houghten, Tetrahedron, 1999, 55, 335.
16. B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415; I. A. Nash, B. W. Bycroft and W. C. Chan, Tetrahedron Lett., 1996, 37, 2625.
17. B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415; I. A. Nash, B. W. Bycroft and W. C. Chan, Tetrahedron Lett., 1996, 37, 2625.
18. G. Byk, M. Frederic and D. Scherman, Tetrahedron Lett., 1997, 38, 3219; 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.
19. G. Byk, M. Frederic and D. Scherman, Tetrahedron Lett., 1997, 38, 3219; 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.
20. 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.
21. B. Carboni, M. Vaultier and R. Carrie, Tetrahedron, 1987, 43, 1799.
22. R. Madsen, C. Roberts and B. Fraser-Reid, J. Org. Chem., 1995, 60, 7920.
23. D. M. Dixit and C. C. Leznoff, J. Chem. Soc., Chem. Commun., 1977, 798.
24. G. C. Look, C. P. Holmes, J. P. Chinn and M. A. Gallop, J. Org. Chem., 1994, 59, 7588.
25. N. M. Kahn, V. Arumugam and S. Balasubramanian, Tetrahedron Lett., 1996, 37, 4819; E. E. Swayze, Tetrahedron Lett., 1997, 38, 8465 and 8643.
26. N. M. Kahn, V. Arumugam and S. Balasubramanian, Tetrahedron Lett., 1996, 37, 4819; E. E. Swayze, Tetrahedron Lett., 1997, 38, 8465 and 8643.
27. B. Carboni, A. Benalil and M. Vaultier, J. Org. Chem., 1993, 58, 3736.
28. R. P. Iyer, D. Yu, N. H. Ho, T. Devlin and S. Agrawal, J. Org. Chem., 1995, 60, 8132; I. Habus, J. Xie, R. P. Iyer, W.-Q. Zhou, L. X. Shen and S. Agrawal, Bioconjugate Chem., 1998, 9, 283.
29. R. P. Iyer, D. Yu, N. H. Ho, T. Devlin and S. Agrawal, J. Org. Chem., 1995, 60, 8132; I. Habus, J. Xie, R. P. Iyer, W.-Q. Zhou, L. X. Shen and S. Agrawal, Bioconjugate Chem., 1998, 9, 283.