Toward understanding how the lactone moiety of discodermolide affects activity

Journal of the American Chemical Society

Volumn 127, Issue 18, 2005, Pages 6532-6533

  Shaw, Simon J ^a   Sundermann, Kurt F ^a   Burlingame, Mark A ^a   Myles, David C ^a   Freeze, B Scott ^b   Xian, Ming ^b   Brouard, Ignacio ^b   Smith III, Amos B ^b  

^a KOSAN BIOSCIENCES INC   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 ANHYDRODISCODERMOLIDE; BUTYROLACTONE; DISCODERMOLIDE; LACTONE; NANOPARTICLE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; SYNTHESIS;

ALKANES; ANTINEOPLASTIC AGENTS; CARBAMATES; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; LACTONES; MOLECULAR CONFORMATION; PYRONES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 18644385908     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051185i     Document Type: Article

References (33)

1. Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. J. Org. Chem. 1990, 55, 4912-4915. Correction J. Org. Chem. 1991, 56, 1346.
2. (a) ter Harr, E.; Kowalski, R. J.; Hammel, E.; Lin, C. M.; Longley, R. E.; Gunasekera, S. P.; Rosenkranz, H. S.; Day, B. W. Biochemistry 1996, 35, 243-250.
3. (b) Hung, D. T.; Chen, J.; Schrieber, S. L. Chem. Biol. 1996, 3, 287-293.
4. (a) Nerenberg, J. B.; Hung, D. T.; Somers, P. K.; Schrieber, S. L. J. Am. Chem. Soc. 1993, 115, 12621-12622.
5. (b) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011-12012.
6. (c) Harried, S. S.; Yang, G.; Strawn, M. A.; Myles, D. C. J. Org. Chem. 1997, 62, 6098-6099.
7. (d) Marshall, J. A.; Johns, B. A. J. Org. Chem. 1998, 63, 7885-7892.
8. (e) Smith, A. B., III; Kaufman, M. D.; Beauchamp, T. J.; LaMarche, M. J.; Arimoto, H. Org. Lett. 1999, 1, 1823-1826.
9. (e) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. Angew. Chem., Int. Ed. 2000, 39, 377-380.
10. (f) Smith, A. B., III; Beauchamp, T. J.; LaMarche, M. J.; Kaufman, M. D.; Qiu, Y.; Arimoto, H.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 2000, 122, 8654-8664.
11. (g) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J.; Serenig, N. J. Am. Chem. Soc. 2001, 123, 9535-9544.
12. (h) Harried, S. S.; Lee, C. P.; Yang, G.; Lee, T. H. I.; Myles, D. C. J. Org. Chem. 2003, 68, 6646-6660.
13. (i) Paterson, I.; Delgado, O.; Florence, G. J.; Lyothier, I.; Scott, J.; Serenig, N. Org. Lett. 2003, 5, 35-38.
14. (j) Smith, A. B., III; Freeze, B. S.; Brouard, I.; Hirose, T Org. Lett. 2003, 5, 4405-4408.
15. Mickel, S. J. et al. Org. Proc. Res. Dev. 2004, 8, 92-130.
16. For recent improvements to the Paterson and Smith syntheses, respectively, see; (a) Paterson, I.; Lyothier, I. Org. Lett. 2004, 6, 4933-4936.
17. (b) Smith, A. B., III; Freeze, B. S.; Xian, M.; Hirose, T. Org. Lett. 2005, 7, 1825-1828.
18. (a) Kinder, F. R., Jr. et al. Abstracts of Papers, 224th National Meeting of the American Chemical Society, Boston, MA, Aug 18-22, 2002; American Chemical Society: Washington, DC, 2002; MEDI 236.
19. (b) Chen, W.; Blair, K. W.; Lassota, P. T.; Ramsey, T. M.; Sorensen, E.; Wang, R. M.; Kinder, F. R., Jr. Abstracts of Papers, 224th National Meeting of the American Chemical Society, Boston, MA, Aug 18-22, 2002; American Chemical Society: Washington, DC, 2002; ORGN 790.
20. (c) Palermo, M. G.; Blair, K. W.; Chen, W.; Guo, Q.; Lassota, P. T.; Ramsey, T. M.; Sorensen, E.; Wang, R. M.; Kinder, F. R., Jr. Abstracts of Papers, 224th National Meeting of the American Chemical Society, Boston, MA, Aug 18-22, 2002; American Chemical Society: Washington, DC, 2002; ORGN 791.
21. (d) Gunasekera, S. P.; Mickel, S. J.; Daeffler, R.; Niederer, D.; Wright, A. E.; Linley, P.; Pitts, T. J. Nat. Prod. 2004, 67, 749-756.
22. (a) Curran, D. P.; Furukawa, T. Org. Lett. 2002, 4, 2233-2236.
23. (b) Choy, N.; Shin, Y.; Nguyen, P. Q.; Curran, D. P.; Balachandran, R.; Madiraju, C.; Day, B. W. J. Med. Chem. 2003, 46, 2846-2864.
24. (c) Minguez, J. M.; Kim, S.-Y.; Giuliano, K. A.; Balachandran, R.; Madiraju, C.; Day, B. W.; Curran, D. P. Bioorg. Med. Chem. 2003, 11, 3335-3357.
25. (a) Paterson, I.; Florence, G. J. Tetrahedron Lett. 2000, 41, 6935-6939.
26. (b) Paterson, I.; Delgado, O. Tetrahedron Lett. 2003, 44, 8877-8882.
27. (a) Martello, L. A.; LaMarche, M. J.; He, L.; Beauchamp, T. J.; Smith, A. B., III; Horwitz, S. B. Chem. Biol. 2001, 8, 843-855.
28. (b) Burlingame, M. A. et al. Bioorg. Med. Chem. Lett. 2004, 14, 2335-2338.
29. (c) Smith, A. B., III et al. Org. Lett. 2005, 7, 311-314.
30. (d) Smith, A. B., III et al. Org. Lett. 2005, 7, 315-318.
31. Smith, A. B., III; LaMarche, M. J.; Falcone-Hindley, M. Org. Lett. 2001, 3, 695-698.
32. Monteagudo, E.; Cicero, D. O.; Comett, B.; Myles, D. C.; Snyder, J. P. J. Am. Chem. Soc. 2001, 723, 6929-6930.
33. Evans, D. A.; Champan, K. T.; Careirra, E. M. J. Am. Chem. Soc. 1998, 770, 3560-3578.