Stereochemical variations on the colchicine motif. Part 4. A remote metalation approach toward a colchicine analog with a five-membered B-ring

Acta Chemica Scandinavica

Volumn 52, Issue 12, 1998, Pages 1380-1385

  Berg, Ulf ^a   Bladh, Håkan ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

COLCHICINE; DRUG DERIVATIVE; TUBULIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; THERMODYNAMICS;

COLCHICINE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM; THERMODYNAMICS; TUBULIN;

EID: 0032245904     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.52-1380     Document Type: Article

References (39)

1. Earlier work: (a) Berg, U., Deinum, J., Lincoln, P. and Kvassman, J. Bioorg. Chem. 19 (1991) 53. (b) Berg, U., Bladh, H., Hoff, M. and Svensson, C. J. Chem. Soc., Perkin Trans 2 (1997) 1697. (c) Berg, U., Bladh, H., Svensson, C. and Wallin, M. Bioorg. Med. Chem. Lett. 7 (1997) 2771.
2. Earlier work: (a) Berg, U., Deinum, J., Lincoln, P. and Kvassman, J. Bioorg. Chem. 19 (1991) 53. (b) Berg, U., Bladh, H., Hoff, M. and Svensson, C. J. Chem. Soc., Perkin Trans 2 (1997) 1697. (c) Berg, U., Bladh, H., Svensson, C. and Wallin, M. Bioorg. Med. Chem. Lett. 7 (1997) 2771.
3. Earlier work: (a) Berg, U., Deinum, J., Lincoln, P. and Kvassman, J. Bioorg. Chem. 19 (1991) 53. (b) Berg, U., Bladh, H., Hoff, M. and Svensson, C. J. Chem. Soc., Perkin Trans 2 (1997) 1697. (c) Berg, U., Bladh, H., Svensson, C. and Wallin, M. Bioorg. Med. Chem. Lett. 7 (1997) 2771.
4. (a) Capraro, H.-G. and Brossi, A. In: Brossi, A., Ed., The Alkaloids, Academic Press, New York 1984, Vol. 23, p. 1.
5. (b) Boyé, O. and Brossi, A. In: Brossi, A., Ed., The Alkaloids, Academic Press, New York 1992, Vol. 41, p. 125.
6. (c) Hastie, S. B. Pharmac. Ther. 51 (1991) 377.
7. (d) Guha, S. and Bhattacharyya, B. Current Science 73 (1997) 351.
8. Medrano, F. J., Andreu, J. M., Gorbunoff, M. J. and Timasheff, S. N. Biochemistry 28 (1989) 5589.
9. (a)Sun, L., McPhail, A. T., Hamel, E., Lin, C. M., Hastie, S. B., Chang, J-J. and Lee, K-H. Med Chem. 36 (1993) 544.
10. (b) Lincoln, P., Nordh, J., Deinum, J., Ångström, J. and Nordén, B. Biochemistry 30 (1991) 1179.
11. Fu, J-M., Zhao, B-P., Sharp, M. J. and Snieckus, V. J. Org. Chem. 56 (1991) 1683.
12. Maddaford, S. P. and Keay, B. A. J. Org. Chem. 59 (1994) 6501.
13. (a) Pietra, F. Acc. Chem. Res. 12 (1979) 132.
14. (b) Biggi, G., de Hoog, A. J., Del Cima, F. and Pietra, F. J. Am. Chem. Soc. 95 (1973) 7108.
15. (c) Cavazza, M. and Pietra, F. J. Chem. Soc., Perkin Trans 1 (1995) 2657.
16. Stirling, C. J. M. Acc. Chem. Res. 9 (1976) 19.
17. Oki, M. Applications of Dynamic NMR Spectroscopy to Organic Chemistry, VCH, Deerfield Beach, Florida 1985.
18. Berg, U., Grimaud, M., and Sandström, J. Nouv. J. Chim. 3 (1979) 175.
19. (a) Bedford, G. R., Greatbanks, D. and Rogers, D. B. Chem. Commun. (1966) 330.
20. (b) Berg, U., Sandström, S., Jennings, W. B. and Randall, D. J. Chem. Soc., Perkin Trans 2 (1980) 949.
21. (a) Pettersson, I. and Berg U. J. Chem. Res. (S) (1984) 208.
22. (b) Hall, D. M. and Harris, M. M. J. Chem. Soc. (1960) 490.
23. (c) Cooke, A. S. and Harris, M. M. J. Chem. Soc. (1963) 2365.
24. (d) Bader, Y., Cooke, A. S. and Harris, M. M. J. Chem. Soc. (1965) 1412.
25. (e) Bott, G., Field, L. D. and Sternhell, S. J. Am. Chem. Soc. 102 (1980) 5618.
26. Sandström, J. Dynamic NMR Spectroscopy, Academic Press, London and New York 1982.
27. Preparation of bovine brain tubulin and microtubule associated proteins and turbidity measurements were performed according to: de Pereda, J. M., Wallin, M., Billger, M. and Andreu, J. M. Cell Motil. Cytoskeleton 30 (1995) 153.
28. Van Geet, A. L. Anal. Chem. (a) 40 (1968) 2227; (b) 42 (1970) 679.
29. Van Geet, A. L. Anal. Chem. (a) 40 (1968) 2227; (b) 42 (1970) 679.
30. Van Geet, A. L. Anal. Chem. (a) 40 (1968) 2227; (b) 42 (1970) 679.
31. McConnell, H. M. J. Chem. Phys. 28 (1958) 430.
32. Berg, U. and Sjöstrand, U. Org. Magn. Reson. 11 (1978) 557.
33. Ref. 13, p. 108.
34. (a) Burkert, U. and Allinger, N. L. Molecular Mechanics; American Chemical Society; Washington, DC 1982.
35. (b) Liljefors, T. and Allinger, N. L. J. Comput. Chem. 6 (1985) 478.
36. (c) Liljefors, T., Tai, J., Li, S. and Allinger, N. L. J. Comput. Chem. 8 (1987) 1051.
37. (a) Liljefors, T. J. Mol. Graphics 1 (1983) 111.
38. (b) Von der Lieth, C. W., Carter, R. E., Dolata, D. P. and Liljefors, T. J. Mol. Graphics 2 (1984) 117; the Macintosh version of MIMIC is available from InStar Software AB, Ideon Research Park, S-223 70 Lund, Sweden.
39. Banwell, M. G. and Onrust, R. Tetrahedron Lett. 26 (1985) 4543.