Conformational studies and solution structure of laulimalide and simplified analogues using NMR spectroscopy and molecular modelling

Tetrahedron Letters

Volumn 46, Issue 21, 2005, Pages 3677-3682

  Paterson, Ian ^a   Menche, Dirk ^a   Britton, Robert ^a   Håkansson, Anders E ^a   Silva Martínez, María Á ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Analogues; Anti cancer agent; Conformational analysis; Laulimalide; Modelling; Solution structure

Indexed keywords

LAULIMALIDE;

ARTICLE; CELL PROLIFERATION; DRUG ACTIVITY; DRUG CONFORMATION; DRUG STRUCTURE; MOLECULAR DYNAMICS; MOLECULAR MODEL; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 17944377638     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.149     Document Type: Article

References (42)

1. E. Quinoa, Y. Kakou, and P. Crews J. Org. Chem. 53 1988 3642
2. D.G. Corley, R. Herb, R.E. Moore, P.J. Scheuer, and V.J. Paul J. Org. Chem. 53 1988 3644
3. C.W. Jefford, G. Bernardinelli, J. Tanaka, and T. Higa Tetrahedron Lett. 37 1996 159
4. For reviews, see: M.T. Crimmins Curr. Opin. Drug Discovery Dev. 5 2002 944
5. J. Mulzer, and E. Öhler Chem. Rev. 103 2003 3753
6. S.L. Mooberry, G. Tien, A.H. Hernandez, A. Plubrukarn, and B.S. Davidson Cancer Res. 59 1999 653
7. G.M. Cragg, and D.J. Newman J. Nat. Prod. 67 2004 232
8. For an in silico approach to predicting the binding site for laulimalide, see: O. Pineda, J. Farràs, L. Maccari, F. Manetti, M. Botta, and J. Vilarrasa Bioorg. Med. Chem. Lett. 14 2004 4825
9. D.E. Pryor, A. O'Brate, G. Bilcer, J.F. Diaz, Yu. Wang, Yo. Wang, M. Kabaki, M.K. Jung, J.M. Andreu, A.K. Ghosh, P. Giannakakou, and E. Hamel Biochemistry 41 2002 9109
10. Peloruside has recently been found to bind to the same site as laulimalide: T.N. Gaitanos, R.M. Buey, J.F. Diaz, P.T. Northcote, P. Teesdale-Spittle, J.M. Andreu, and J.H. Miller Cancer Res. 64 2004 5063
11. A.K. Ghosh, and Y. Wang J. Am. Chem. Soc. 122 2000 11027
12. A.K. Ghosh, Y. Wang, and J.T. Kim J. Org. Chem. 66 2001 8973
13. I. Paterson, C. De Savi, and M. Tudge Org. Lett. 3 2001 213
14. I. Paterson, C. De Savi, and M. Tudge Org. Lett. 3 2001 3149
15. J. Mulzer, and E. Öhler Angew. Chem., Int. Ed. 40 2001 3843
16. V.S. Evev, H. Kaehlig, and J. Mulzer J. Am. Chem. Soc. 123 2001 10764
17. M.T. Crimmins, M.G. Stanton, and S.P. Allwein J. Am. Chem. Soc. 124 2002 5958
18. D.R. Williams, L. Mi, R.J. Mullins, and R.E. Stites Tetrahedron Lett. 43 2002 4841
19. S.G. Nelson, W.S. Chueng, A.J. Kassick, and M.A. Hilfiker J. Am. Chem. Soc. 124 2002 13654
20. P.A. Wender, S.G. Hegde, R.D. Hubbard, and L. Zhang J. Am. Chem. Soc. 124 2002 4956
21. A. Ahmed, K. Hoegenauer, V.S. Enev, M. Hanbauer, H. Kaehlig, E. Öhler, and J. Mulzer J. Org. Chem. 68 2003 3026
22. P.A. Wender, S.G. Hegde, R.D. Hubbard, L. Zhang, and S.L. Mooberry Org. Lett. 5 2003 3507
23. B.M. Gallagher Jr., F.G. Fang, C.W. Johannes, M. Pesant, M.R. Tremblay, H. Zhao, K. Akasaka, X.-y. Li, J. Liu, and B.A. Littlefield Bioorg. Med. Chem. Lett. 14 2004 575
24. I. Paterson, H. Bergmann, D. Menche, and A. Berkessel Org. Lett. 6 2004 1293
25. S.L. Mooberry, D.A. Randall-Hlubek, R.M. Leal, S.G. Hegde, R.D. Hubbard, L. Zhang, and P.A. Wender Proc. Natl. Acad. Sci. U.S.A. 101 2004 8803
26. Gallagher, B. M., Jr; Zhao, H.; Pesant, M.; Fang, F. G. Tetrahedron Lett
27. Paterson, I.; Menche, D.; Håkansson, A. E.; Longstaff, A.; Wong, D.; Barasoain, I.; Buey, R. M.; DIÍaz, J. F. Bioorg. Med. Chem. Lett., accepted for publication
28. For some selected examples, see: R.E. Taylor, and J. Zajicek J. Org. Chem. 64 1999 7224
29. J.P. Snyder, N. Nevins, D.O. Cicero, and J. Jansen J. Am. Chem. Soc. 122 2000 724
30. A.B. Smith III, M.J. LaMarche, and M. Falcone-Hindley Org. Lett. 3 2001 695
31. E. Monteagudo, D.O. Cicero, B. Cornett, D.C. Myles, and J.P. Snyder J. Am. Chem. Soc. 123 2001 16929
32. I. Paterson, R. Britton, O. Delgado, and A.E. Wright Chem. Commun. 6 2004 632
33. 1c
34. 8g
35. T.R. Hoye, P.R. Hanson, and J.R. Vyvyan J. Org. Chem. 59 1994 4096
36. T.R. Hoye, and H. Zhao J. Org. Chem. 67 2002 4014
37. 1c which suggest that laulimalide also adopts a similar conformation in these solvents
38. F. Mohamadi, N.G.J. Richards, W.C. Guida, R. Kiskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, and W.C. Still J. Comput. Chem. 11 1990 440
39. W.C. Still, A. Tempczyk, R.C. Hawley, and Hendrickson J. Am. Chem. Soc. 112 1990 6127
40. -1 lower in energy
41. A. Berkessel, D. Menche, C. Sklorz, M. Schröder, and I. Paterson Angew. Chem., Int. Ed. 42 2003 1032
42. For a related approach along these lines, see Ref. 8f