Direct C-11 functionalisation of anatoxin-a. Application to the synthesis of new ligand-based structural probes

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 16, 1997, Pages 2313-2318

  Magnus, Nicholas A ^a   Ducry, Laurent ^a   Rolland, Valérie ^a   Wonnacott, Susan ^b   Gallagher, Timothy ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF BATH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748649334     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a702087b     Document Type: Article

References (45)

1. J. P. Devlin, O. E. Edwards, P. R. Gorham, N. R. Hunter, R. K. Pike and B. Stavric, Can. J. Chem., 1977, 55, 1367.
2. B. Badio, H. M. Garraffo, T. F. Spande and J. W. Daly, Med. Chem. Res., 1994, 4, 440;
3. T. F. Spande, H. M. Garraffo, M. W. Edwards, H. J. C. Yeh, L. Pannell and J. W. Daly, J. Am. Chem. Soc., 1992, 114, 3475.
4. For the assignment of the absolute stereochemistry of 2, see S. R. Fletcher, R. Baker, M. S. Chambers, R. H. Herbert, S. C. Hobbs, S. R. Thomas, H. M. Verrier, A. P. Watt and R. G. Ball, J. Org. Chem., 1994, 59, 1771.
5. For studies indicating 2 to be a nicotinic agonist, see B. Badio and J. W. Daly, Mol. Pharmacol., 1994, 45, 563;
6. B. Badio, D. Shi, H. M. Garraffo and J. W. Daly, Drug. Dev. Res., 1995, 36, 46.
7. P. Thomas, M. Stephens, G. Wilkie, M. Amar, G. G. Lunt, P. Whiting, T. Gallagher, E. Pereira, M. Alkondon, E. X. Albuquerque and S. Wonnacott, J. Neurochem., 1993, 60, 2308;
8. P. Thomas, P. A. Brough, T. Gallagher and S. Wonnacott, Drug Dev. Res., 1994, 31, 147.
9. For a review of synthetic approaches to anatoxin-a, see H. L. Mansell, Tetrahedron, 1996, 52, 6025.
10. Also see P. J. Parsons, N. P. Camp, J. M. Underwood and D. M. Harvey, Tetrahedron, 1996, 52, 11637.
11. For the most recent synthetic work directed towards epibatidine and analogues, see B. M. Trost and G. R. Cook, Tetrahedron Lett., 1996, 37, 7485;
12. C. Szántay, Z. Kardos-Balogh, I. Moldvai, C. Szántay Jr., E. Temesvári-Major and G. Blaskó, Tetrahedron, 1996, 52, 11 053;
13. C. Zhang and M. T. Trudell, J. Org. Chem., 1996, 61, 7189;
14. J. R. Malpass, D. A. Hemmings and A. L. Wallis, Tetrahedron Lett., 1996, 37, 3911;
15. D. Bai, R. Xu, G. Chu and X. Zhu, J. Org. Chem., 1996, 61, 4600.
16. M. W. Holladay, S. A. Lebold and N.-H. Lin, Drug Dev. Res., 1995, 35, 191.
17. (a) F. J. Sardina, M. H. Howard, M. Morningstar and H. Rapoport, J. Org. Chem., 1990, 55, 5025;
18. (b) M. H. Howard, F. J. Sardina and H. Rapoport, J. Org. Chem., 1990, 55, 2829;
19. (c) F. J. Sardina, M. H. Howard, A. M. P. Koskinen and H. Rapoport, J. Org. Chem., 1989, 54, 4654;
20. (d) A. M. P. Koskinen and H. Rapoport, J. Med. Chem., 1985, 28, 1301;
21. (e) J. S. Petersen, G. Fels and H. Rapoport, J. Am. Chem. Soc., 1984, 106, 4539;
22. (f) J. S. Petersen, S. Töteberg-Kaulen and H. Rapoport, J. Org. Chem., 1984, 49, 2948.
23. For structure-activity relationships relating to anatoxin-a, see S. Wonnacott, S. Jackman, K. L. Swanson, H. Rapoport and E. X. Albuquerque, J. Pharmacol. Exp. Ther., 1991, 259, 387;
24. K. L. Swanson, R. S. Aronstam, S. Wonnacott, H. Rapoport and E. X. Albuquerque, J. Pharmacol. Exp. Ther., 1991, 259, 377;
25. K. L. Swanson, Y. Aracava, F. J. Sardina, H. Rapoport, R. S. Aronstam and E. X. Albuquerque, Mol. Pharmacol., 1989, 35, 233;
26. K. L. Swanson, C. N. Allen, R. S. Aronstam, H. Rapoport and E. X. Albuquerque, Mol. Pharmacol., 1986, 29, 250.
27. For computational studies aimed at the structure-activity relationships associated with anatoxin-a and derivatives, see D. T. Manallack, D. D. Ellis, P. E. Thompson, T. Gallagher and D. J. Livingstone, Nat. Prod. Lett., 1994, 4, 121;
28. D. T. Manallack, T. Gallagher and D. J. Livingstone, in Neural Networks in QSA R and Drug Design, ed. J. Devillers, Academic Press, London, 1996, p. 177.
29. D. B. Kanne, D. J. Ashworth, M. T. Cheng, L. C. Mutter and L. G. Abood, J. Am. Chem. Soc., 1986, 108, 7864;
30. D. B. Kanne and L. G. Abood, J. Med. Chem., 1988, 31, 506.
31. P. A. Brough, T. Gallagher, P. Thomas, S. Wonnacott, R. Baker, K. M. A. Malik and M. B. Hursthouse, J. Chem. Soc., Chem. Commun., 1992, 1087.
32. For other studies focused on the biological significance of enone conformation, see: P. Thomson, D. T. Manallack, F. E. Blaney and T. Gallagher, J. Comput. Aided Mol. Des., 1992, 287;
33. U. Hacksell and C. Mellin, Prog. Brain Res., 1989, 79, 95.
34. A. Hernandez and H. Rapoport, J. Org. Chem., 1994, 59, 1058.
35. For the application of dansylated acetylcholine derivatives, see: T. Heidmann and J. P. Changeux, Eur. J. Biochem., 1979, 94, 281;
36. T. Heidmann and J. P. Changeux, Biochem. Biophys. Res. Commun., 1980, 97, 889.
37. P. Kofuji, Y. Aracava, K. L. Swanson, R. S. Aronstam, H. Rapoport and E. X. Albuquerque, J. Pharmacol. Exp. Ther., 1990, 252, 517;
38. D. K. Stevens and R. I. Krieger, Toxicon, 1990, 28, 133;
39. N,N-dimethylanatoxin-a has also been evaluated: A. C. S. Costa, K. L. Swanson, Y. Aracava, R. S. Aronstam and E. X. Albuquerque, J. Pharmacol. Exp. Ther., 1990, 252, 507.
40. N. J. S. Huby, P. Thompson, S. Wonnacott and T. Gallagher, J. Chem. Soc., Chem. Commun., 1991, 243.
41. S. Wonnacott, K. L. Swanson, E. X. Albuquerque, N. J. S. Huby, P. Thompson and T. Gallagher, Biochem. Pharmacol., 1992, 43, 419.
42. 15 has also been isolated as a natural product: O. M. Skulberg, W. W. Carmichael, R. A. Anderson, S. Matsunaga, R. E. Moore and R. Skulberg, Environ. Toxicol. Chem., 1992, 11, 321.
43. G. F. Koser, A. G. Relenyi, A. N. Kalos, L. Rebrovic and R. H. Wettach, J. Org. Chem., 1982, 47, 2487.
44. P. A. Brough, PhD Thesis, University of Bristol, 1994.
45. N. Seiler, T. Schmidt-Glenewinkel and H. H. Schneider J. Chromatogr., 1973, 84, 95.