Stereochemical variations on the colchicine motif. Part 2.1 Unexpected tetracyclic isoxazole derivatives

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 9, 1997, Pages 1697-1704

  Berg, Ulf ^a   Bladh, Håkan ^a   Hoff, Maria ^a   Svensson, Christer ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000449776     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a701400g     Document Type: Article

References (50)

1. Part 1: see ref. 3.
2. (a) H.-G. Capraro and A. Brossi, Tropolonic Colchicum Alkaloids, in The Alkaloids, ed. A. Brossi, Academic Press, New York, 1984, vol. 23, p. 1:
3. (b) O. Boyé and A. Brossi, Tropolonic Colchicum Alkaloids, in The Alkaloids, ed. A. Brossi, Academic Press, New York, 1992, vol. 41, p. 125;
4. (c) S. Bane Hastie, Pharm. Ther., 1991, 51, 377.
5. U. Berg, J. Deinum, P. Lincoln and J. Kvassman, Bioorg. Chem., 1991, 19, 53.
6. H. W. Detrich, III, R. C. Williams, Jr., T. L. Macdonald, L. Wilson and D. Puett, Biochemistry, 1981, 21, 5999.
7. S. Bane Hastie and R. P. Rava, J. Am. Chem. Soc., 1989, 111, 6993.
8. P. Lincoln, J. Nordh, J. Deinum, J. Ångström and B. Nordén, Biochemistry, 1991, 30, 1179.
9. U. Berg and H. Bladh, to be published.
10. The structure of the isomer 4b was established by X-ray diffraction; to be published.
11. V. Prelog and G. Helmchen, Angew. Chem., Int. Ed. Engl., 1982, 21, 567.
12. A. Bondi, J. Phys. Chem., 1964, 68, 441.
13. C. Koerntgen and T. N. Margulis, J. Pharm. Sci., 1977, 66, 1232.
14. M. G. Banwell, S. C. Peters, R. J. Greenwood, M. F. Mackay, E. Hamel and C. M. Lin, Aust. J. Chem., 1992, 45, 1577.
15. Cambridge Structural Database, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, UK CB2 IEZ.
16. R. Dumont, A. Brossi and J. V. Silverton, J. Org. Chem., 1986, 51, 2515.
17. C. Koerntgen and T. N. Margulis, J. Pharm. Sci., 1977, 66, 1127.
18. T. H. Al-Tel, M. H. AbuZarga, S. S. Sabri, A. J. Freyer and M. Shamma, J. Nat. Prod., 1990, 53, 623.
19. M. Oki, Application of Dynamic NMR Spedroscopy to Organic Chemistry, VCH Publishers. Deerfield Beach, 1985, p. 141, and references therein.
20. Tropone and several of its derivatives are planar in the gas-phase and the vibrational spectrum of tropone in the gas phase confirms the inherent floppyness of the ring; see, R. L. Redington, S. A. Latimer and C. W. Bock, J. Phys. Chem., 1990, 94, 163, and references therein. These structural features are well reproduced by calculations with the MM2(85) force field but not by the MM2(77) or MMX force field.
21. L. Lessinger and T. N. Margulis, Acta Crystallogr., Sect. B, 1978, 34, 578.
22. L. Lessinger and T. N. Margulis, Acta Crystallogr., Sect. B, 1978, 34, 1556.
23. U. Berg, H. Bladh, B. Dahllöf, C. Ekström and B. Hartley-Asp, to be published.
24. B. Dahllöf. A. Billström, F. Cabral and B. Hartley-Asp, Cancer Res., 1993, 53, 4573.
25. (a) G. G. Choudhury, A. Banerjee, B. Bhattacharyya and B. B. Biwas, FEBS Lett., 1983, 161, 55;
26. (b) S. Bane, D. Puett, T. L. Macdonald and R. C. Williams, J. Biol. Chem., 1984, 259, 7391;
27. (c) J. M. Andreu, M. J. Gorbunoff, J. C. Lee and S. N. Timasheff, Biochemistry, 1984, 23, 1742;
28. (d) B. Bhattacharyya, R. Howard, S. N. Maity, A. Brossi, P N. Sharma and J. Wolff, Proc. Natl. Acad. Sci. USA, 1986, 83, 2052;
29. (e) Y. Engelborghs and T. J. Fitzgerald, J. Biol. Chem., 1987, 262, 5204;
30. (f) A. Banerjee, L. D. Barnes and R. F. Ludena, Biochem. Biophys. Acta, 1987, 913, 138;
31. (g) E. A. Pyles and S. Bane Hastie, Biochemistry, 1993, 32, 2329.
32. J. R. Dahl, M. E. Staretz, J. L. Potenziano and S. B. Hastie, Electronic poster, 1996, http://chemiris.chem.binghamton.edu: 8080/HASTIE/QSAR.POSTER/qsar.poster.html
33. C. Svensson and B. Sommarin, Acta Crystallogr., Sect. A, 1993, 49, Suppl., 20.
34. TEXSAN: Single Crystal Structure Analysis Software, version 1.7, Molecular Structure Corporation, The Woodlands, Texas, 1994.
35. International Tables fur X-Ray Crystallography, ed. J. A. Ibers and W. C. Hamilton, Kynoch Press, Birmingham, 1974, vol. IV.
36. J. Sandström. Dynamic NMR Spectmscopy, Academic Press, London, 1982, 66.
37. A. L. Van Geet, Anal. Chem., (a) 1968, 40, 2227; (b) 1970, 42, 679.
38. A. L. Van Geet, Anal. Chem., (a) 1968, 40, 2227; (b) 1970, 42, 679.
39. H. M. McConnel, J. Chem. Phys., 1958, 28, 430.
40. D. S. Stephensen and G. Binsch, Quantum Chemistry Program Exchange, 1978, 11, 365.
41. U. Berg and U. Sjöstrand, Org. Magn. Reson., 1978, 11, 557.
42. S. Glasstone, K. J. Laidler and H. Eyring, Theory of Rate Processes, McGraw-Hill, New York, 1941, 195.
43. Ref. 28. p. 108.
44. (a) U. Burkert and N. L. Allinger, Molecular Mechanics, American Chemical Society, Washington, DC, 1982;
45. (b) T. Liljefors and N. L. Allinger, J. Comput. Chem., 1985, 6, 478;
46. (c) T. Liljefors, J. Tai, S. Li and N. L. Allinger, J. Comput. Chem., 1987, 8, 1051.
47. (a) T. Liljefors, J. Mol. Graphics, 1983, 1, 111;
48. (b) C. W. Von der Lieth, R. E. Carter, D. P. Dolata and T. Liljefors, J. Mol. Graphics, 1984, 2, 117; the Macintosh version of MIMIC is available from InStar Software AB, Ideon Research Park, S-223 70 Lund, Sweden.
49. M. Rossi, J. Link and J. C. Lee, Arch. Biochem. Biophys., 1984, 231, 470.
50. A. A. Bothner-By, Adv. Magn. Reson., 1965, 1, 195.