Molecular modeling, total synthesis, and biological evaluations of c9-deoxy bryostatin 1

Angewandte Chemie - International Edition

Volumn 49, Issue 27, 2010, Pages 4580-4584

  Keck, Gary E ^a   Poudel, Yam B ^a   Rudra, Arnab ^a   Stephens, Jeffrey C ^a   Kedei, Noemi ^b   Lewin, Nancy E ^b   Peach, Megan L ^c   Blumberg, Peter M ^b  

^a UNIVERSITY OF UTAH   (United States)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

^c SAIC FREDERICK INC   (United States)

Author keywords

Biological activity cancer; Natural products structure activity relationships; Total synthesis

Indexed keywords

BIOLOGICAL ACTIVITIES; BIOLOGICAL EFFECTS; BIOLOGICAL EVALUATION; BIOLOGICAL FUNCTIONS; BRYOSTATIN 1; CHEMICAL EQUATIONS; HYDROGEN BONDINGS; LEUKEMIA CELLS; LNCAP CELLS; NATURAL PRODUCTS; PROTEIN KINASE C; STRUCTURE ACTIVITY RELATIONSHIPS; TITLE COMPOUNDS; TOTAL SYNTHESIS;

BIOACTIVITY; MOLECULAR MODELING;

PROTEINS;

BRYOSTATIN; BRYOSTATIN 1; OXYGEN; PROTEIN KINASE C DELTA;

ARTICLE; CELL ADHESION; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HUMAN; SYNTHESIS; TUMOR CELL LINE;

BRYOSTATINS; CELL ADHESION; CELL LINE, TUMOR; CELL PROLIFERATION; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXYGEN; PROTEIN KINASE C-DELTA;

EID: 77953953493     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201001200     Document Type: Article

References (38)

1. For reviews of the bryostatins and bryostatin analogues, see: a) K. J. Hale, M. G. Hummersome, S. Manaviazar, M. Frigerio, Nat. Prod. Rep. 2002, 19, 413-453;
2. b) K. J. Hale, S. Manaviazar, Chem. Asian J. 2010, 5, 704-754.
3. G. R. Pettit, C. L. Herald, D. L. Doubek, D. L. Herald, J. Am. Chem. Soc. 1982, 104, 6846-6848.
4. D. E. Schaufelberger, M. P. Koleck, J. A. Beutler, A. M. Vatakis, A. B. Alvarado, P. Andrews, L. V. Marzo, G. M. Muschik, J. Roach, J.T. Ross, W. B. Lebherz, M. P. Reeves, R. M. Eberwein, L. I. Rodgers, R. P. Testerman, K. M. Snader, S. Forenza, J. Nat. Prod. 1991, 54, 1265-1270.
5. For current information, see http://clinicaltrials.gov.
6. For further information see: http://www.brni.org/news/Press Release42209.htm.
7. M. E. Reyland, P. A. Insel, R. O. Messing, E. C. Dempsey, A. C. Newton, D. Mochly-Rosen, A. P. Fields, Am. J. Physiol. Lung Cell. Mol. Physiol. 2000, 279, 429-438.
8. E. M. Griner, M. G. Kazanietz, Nat. Rev. Cancer 2007, 7, 281-294.
9. P. M. Blumberg, G. R. Pettit in New Leads and Targets in Drug Research (Ed. : P. Krosgaard-Larsen, C. B. Christensen, H. Kodof), Munksgaard, Copenhagen, 1992, pp. 273-285.
10. a) D. A. Evans, P. H. Carter, E. M. Carreira, A. B. Charette, J. A. Prunet, M. Lautens, J. Am. Chem. Soc. 1999, 121, 7540-7552;
11. b) M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408;
12. K. Ohmori, Y. Ogawa, T. Obitsu, Y. Ishikawa, S. Nishiyama, S. Yamamura, Angew. Chem. 2000, 112, 2376-2379;
13. Angew. Chem. Int. Ed. 2000, 39, 2290-2294;
14. S. Manaviazar, M. Frigerio, G. S. Bhatia, M. G. Hummersone, A. E. Aliev, K. J. Hale, Org. Lett. 2006, 8, 4477-4480.
15. B. M. Trost, G. Dong, Nature 2008, 456, 485-488.
16. For leading references, see: a) P. A. Wender, J. DeBrabander, P. G. Harran, J. Jimenez, M. F. T. Koehler, B. Lippa, C. Park, M. Shiozaki, J. Am. Chem Soc. 1998, 120, 4534-4535;
17. b) P. A. Wender, J. L. Baryza, C. E. Bennett, F. C. Bi, S. E. Brenner, M. O. Clarke, J. C. Horan, C. Kan, E. Lacôte, B. S. Lippa, P. G. Nell, T. M. Turner, J. Am. Chem. Soc. 2002, 124, 13648-13649;
18. P. A. Wender, B. A. DeChristopher, A. J. Schreier, J. Am. Chem. Soc 2008, 130, 6658-6659;
19. P. A. Wender, J. L. Baryza, M. K. Hilinski, J. C. Horan, C. Kan, V. A. Verma, Drug Discovery Research: New Frontiers in the Post-Genomic Era (Ed.: Z. Huang), Wiley-VCH, Hoboken, NJ, 2007, pp. 127-162.
20. a) G. E. Keck, A. P. Truong, Org. Lett. 2005, 7, 2149-2152;
21. b) G. E. Keck, A. P. Truong, Org. Lett. 2005, 7, 2153-2156;
22. G. E. Keck, D. S. Welch, P. K. Vivian, Org. Lett 2006, 8, 3667-3670;
23. G. E. Keck, D. S. Welch, Y. B. Poudel, Tetrahedron Lett. 2006, 47, 8267-8270.
24. G. E. Keck, M. B. Kraft, A. P. Truong, W. Li, C. C. Sanchez, N. Kedei, N. E. Lewin, P. M. Blumberg, J. Am. Chem. Soc. 2008, 130, 6660-6661.
25. G. E. Keck, Y. B. Poudel, D. S. Welch, M. B. Kraft, A. P. Truong, J. C. Stephens, N. Kedei, N. E. Lewin, P. M. Blumberg, Org. Lett. 2009, 11, 593-596.
26. K. Kimura, M. Y. Mizutani, N. Tomioka, Y. Endo, K. Shudo, A. Itai, Chem. Pharm. Bull. 1999, 47,1134-1137.
27. Y. Kamano, H. Zhang, H. Morita, H. Itokawa, O. Shirota, G. R. Pettit, D. L. Herald, C. L. Herald, Tetrahedron 1996, 52, 2369-2376.
28. G. G. Zhang, M. G. Kazanietz, P. M. Blumberg, J. H. Hurley, Cell 1995, 81, 917-924.
29. The "Merle numbers" used herein are permanent identifiers for the analogue structures.
30. T. Choi, C. W. Lee, A. K. Chatterjee, R. H. Grubbs, J. Am. Chem. Soc 2001, 123, 10417-10418.
31. K. Tanaka, Y. Ohta, K. Fuji, Tetrahedron Lett. 1993, 34, 4071-4074.
32. M. B. Kraft, University of Utah, unpublished results.
33. J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
34. The use of this hemiacetal in a similar aldol condensation has been previously described. See: J. L. Baryza, Ph.D. Thesis, Stanford University, 2005.
35. B. H. Lipshutz, D. F. Harvey, Synth. Commun. 1982, 14, 267-277.
36. J. A. Vrana, A. M. Saunders, P. C. Srikumar, S. Grant, Differentiation 1998, 63, 33-42.
37. G. E. Keck, W. Li, M. B. Kraft, N. Kedei, N. E. Lewin, P. M. Blumberg, Org. Lett. 2009, 11, 2277-2280.
38. J. E. Gschwend, W. R. Fair, C. T. Powell, Mol. Pharmacol. 2000, 57, 1224-1234.