Functionalization of the alicyclic skeleton of epibatidine: Synthesis and nicotinic acetylcholine receptor binding affinities of epibatidine analogues

Organic and Biomolecular Chemistry

Volumn 1, Issue 22, 2003, Pages 3878-3881

  Wei, Zhi Liang ^a   Xiao, Yingxian ^b   George, Clifford ^c   Kellar, Kenneth J ^b   Kozikowski, Alan P ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b GEORGETOWN UNIVERSITY   (United States)

^c NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; ISOMERS; OXIDATION; SILICA GEL; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

ARYL LITHIUM REAGENT; EPIBATIDINE; EPIMERIZATION; HYDROBORATION; MICHAEL ADDITION; SULFONYL GROUP;

ORGANIC COMPOUNDS;

ANALGESIC AGENT; EPIBATIDINE; FUSED HETEROCYCLIC RINGS; NICOTINIC RECEPTOR; PYRIDINE DERIVATIVE; SILICON;

ANIMAL; ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER ASSISTED EMISSION TOMOGRAPHY; FROGS AND TOADS; KINETICS; METABOLISM; PROTEIN BINDING; SYNTHESIS; X RAY;

ANALGESICS, NON-NARCOTIC; ANIMALS; ANURA; BICYCLO COMPOUNDS, HETEROCYCLIC; KINETICS; MODELS, CHEMICAL; MODELS, MOLECULAR; PROTEIN BINDING; PYRIDINES; RECEPTORS, NICOTINIC; SILICON; TOMOGRAPHY, EMISSION-COMPUTED; X-RAYS;

EID: 0344946187     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b308906a     Document Type: Article

References (50)

1. (a) M. W. Holladay, M. J. Dart and J. K. Lynch, J. Med. Chem., 1997, 40, 4169
2. (b) J. Lindstrom, Mol. Neurobiol., 1997, 15, 193
3. (c) D. Paterson and A. Nordberg, Prog. Neurobiol., 2000, 61, 75
4. (d) G. K. Lloyd and M. Williams, J. Pharmacol. Exp. Ther., 2000, 292, 461.
5. (a) 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
6. (b) J. W. Daly, J. Nat. Prod., 1998, 61, 162.
7. (a) T. C. Li, C. G. Qian, J. Eckman, D. F. Huang and T. Y. Shen, Bioorg. Med. Chem. Lett., 1993, 3, 2759
8. (b) C. G. Qian, T. C. Li, T. Y. Shen, L. Libertine-Garahan, J. Eckman, T. Biftu and S. Ip, Eur. J. Pharmacol., 1993, 250, R13
9. (c) M. Fisher, D. Huangfu, T. Y. Shen and P. G. Guyenet, J. Pharmacol. Exp. Ther., 1994, 270, 702
10. (d) B. Badio and J. W. Daly, Mol. Pharmacol., 1994, 45, 563.
11. B. Badio, H. M. Garraffo, C. V. Plummer, W. L. Padgett and J. W. Daly, Eur. J. Pharmacol., 1997, 321, 189.
12. For the total synthesis of epibatidine, see: (a) A. Palmgren, A. L. E. Larsson, J.-E. B̈ckvall and P. Helquist, J. Org. Chem., 1999, 64, 836
13. (b) D. A. Evans, K. A. Scheidt and C. W. Downey, Org. Lett., 2001, 3, 3009 and references therein.
14. (a) F. Liang, H. A. Navarro, P. Abraham, P. Kotian, Y.-S. Ding, J. Fowler, N. Volkow, M. J. Kuhar and F. I. Carroll, J. Med. Chem., 1997, 40, 2293
15. (b) A. Otten, J. C. Namyslo, M. Stoermer and D. E. Kaufmann, Eur. J. Org. Chem., 1998, 1997
16. (c) J.-P. G. Seerden, M. Th. M. Tulp, H. W. Scheeren and C. G. Kruse, Bioorg. Med. Chem., 1998, 6, 2103
17. (d) J. E. Spang, S. Bertrand, G. Westera, J. T. Patt, P. A. Schubiger and D. Bertrand, Chem. Biol., 2000, 7, 545
18. (e) F. I. Carroll, J. R. Lee, H. A. Navarro, L. F. Brieaddy, P. Abraham, M. I. Damaj and B. R. Martin, J. Med. Chem., 2001, 44, 4039
19. (f) D. Che, T. Wegge, M. T. Stubbs, G. Seitz, H. Meier and C. Methfessel, J. Med. Chem., 2001, 44, 47
20. (g) F. I. Carroll, F. Liang, H. A. Navarro, L. E. Brieaddy, P. Abraham, M. I. Damaj and B. R. Martin, J. Med. Chem., 2001, 44, 2229
21. (h) F. I. Carroll, J. R. Lee, H. A. Navarro, W. Ma, L. E. Brieaddy, P. Abraham, M. I. Damaj and B. R. Martin, J. Med. Chem., 2002, 45, 4755
22. (i) N. Zhang, M. Tomizawa and J. E. Casida, Bioorg. Med. Chem. Lett., 2003, 13, 525
23. (j) C. Che, G. Petit, F. Kotzyba-Hibert, S. Bertrand, D. Bertrand, T. Grutter and M. Goeldner, Bioorg. Med. Chem. Lett., 2003, 13, 1001.
24. (a) A. Kasyan, C. Wagner and M. E. Maier, Tetrahedron, 1998, 54, 8047
25. (b) J. R. Malpass and C. D. Cox, Tetrahedron Lett., 1999, 40, 1419
26. (c) C. D. Cox and J. R. Malpass, Tetrahedron, 1999, 55, 11879
27. (d) C. D. Cox, J. R. Malpass, J. Gordon and A. Rosen, J. Chem. Soc., Perkin Trans. 1, 2001, 2372.
28. (a) D. Bai, R. Xu, G. Chu and X. Zhu, J. Org. Chem., 1996, 61, 4600
29. (b) J. R. Malpass, D. A. Hemmings and A. L. Wallis, Tetrahedron Lett., 1996, 37, 3911
30. (c) E. Wright, T. Gallagher, C. G. V. Sharples and S. Wonnacott, Bioorg. Med. Chem. Lett., 1997, 7, 2867
31. (d) C. Zhang, L. Gyermek and M. L. Trudell, Tetrahedron Lett., 1997, 38, 5619
32. (e) D. Barlocco, G. Cignarella, D. Tondi, P. Vianello, S. Villa, A. Bartolini, C. Ghelardini, N. Galeotti, D. J. Anderson, T. A. Kuntzweiler, D. Colombo and L. Toma, J. Med. Chem., 1998, 41, 674
33. (f) H. F. Olivo, D. A. Colby and M. S. Hemenway, J. Org. Chem., 1999, 64, 4966
34. (g) J. R. Malpass, D. A. Hemmings, A. L. Wallis, S. R. Fletcher and S. Patel, J. Chem. Soc., Perkin Trans. 1, 2001, 1044
35. (h) S. Rádl, P. Hezký, W. Hafner, M. Budešinský and L. Hejnová, Bioorg. Med. Chem. Lett., 2000, 10, 55
36. (i) C. G. V. Sharples, G. Karig, G. L. Simpson, J. A. Spencer, E. Wright, N. S. Millar, S. Wonnacott and T. Gallagher, J. Med. Chem., 2002, 45, 3235
37. (j) H. Gohlke, D. Gündisch, S. Schwarz, G. Seitz, M. C. Tilotta and T. Wegge, J. Med. Chem., 2002, 45, 1064
38. (k) H. Gohlke, S. Schwarz, D. Gündisch, M. C. Tilotta, A. Weber, T. Wegge and G. Seitz, J. Med. Chem., 2003, 46, 2031.
39. Though some potential such ligands have been described during the total synthesis of epibatidine, none of them were deprotectedor pharmacologically investigated. See reference 18a and (a) E. J. Corey, T.-P. Loh, S. AchyuthaRao, D. C. Daley and S. Sarshar, J. Org. Chem., 1993, 58, 5600
40. (b) 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
41. (c) C. Zhang and M. L. Trudell, J. Org. Chem., 1996, 61, 7189
42. (d) H. F. Olivo and M. S. Hemenway, J. Org. Chem., 1999, 64, 8968
43. (e) G. M. P. Giblin, C. D. Jones and N. S. Simpkins, J. Chem. Soc., Perkin Trans. 1, 1998, 3689.
44. Z.-L. Wei, C. George and A. P. Kozikowski, Tetrahedron Lett., 2003, 44, 3847.
45. (a) O. Magidson and G. Menschikoff, Chem. Ber., 1925, 58, 113
46. (b) Y. Hama, Y. Nobuhara, Y. Aso, T. Otsubo and F. Ogura, Bull. Chem. Soc. Jpn., 1988, 61, 1683.
47. int = 0.0395) independent reflections, parameters = 142, goodness-of-fit = 1.036, final R indices [I>2ω(I)] R = 0.0384, Rw = 0.0928.
48. For the base-mediated epimerization of the 2-endo-pyridyl group, see references 9b-d, and C. Szántay, Z. Kardos-Balogh, I. Moldvai, C. Szántay Jr., E. Temesvári-Major and G. Blaskó, Tetrahedron, 1996, 52, 11056.
49. int = 0.0468) independent reflections, parameters = 283, goodness-of-fit = 1.040, final R indices [I>2ω(I)] R, = 0.0477, Rw = 0.1293.
50. Z.-L. Wei, P. A. Petukhov, Y. Xiao, W. Tückmantel, C. George, K. J. Kellar and A. P. Kozikowski, J. Med. Chem., 2003, 46, 291.