A series of 23,24-dihydrodiscodermolide analogues with simplified lactone regions

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 7, 2006, Pages 1961-1964

  Shaw, Simon J ^a   Sundermann, Kurt F ^a   Burlingame, Mark A ^a   Zhang, Dan ^a   Petryka, Joseph ^a   Myles, David C ^a  

^a KOSAN BIOSCIENCES INC   (United States)

Author keywords

Analogues; Antitumor; Discodermolide

Indexed keywords

DISCODERMOLIDE; LACTONE;

ALDOL REACTION; ARTICLE; CELL PROLIFERATION; CONTROLLED STUDY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; GENE MUTATION; HUMAN; HUMAN CELL; WITTIG REACTION;

CELL LINE, TUMOR; HUMANS; LACTONES; TRITERPENES;

EID: 33144486130     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.12.066     Document Type: Article

References (19)

1. S.P. Gunasekera, M. Gunasekera, R.E. Longley, and G.K. Schulte J. Org. Chem. 55 1990 4912
2. Correction J. Org. Chem. 56 1991 1346
3. E. ter Haar, R.J. Kowalski, E. Hamel, C.M. Lin, R.E. Longley, S.P. Gunasekera, H.S. Rosenkranz, and B.W. Day Biochemistry 35 1996 243
4. For a review, see: I. Paterson, and G.J. Florence Eur. J. Org. Chem. 2003 2193
5. S.J. Mickel, G.H. Sedelmeier, D. Niederer, R. Daeffler, A. Osmani, K. Schreiner, M. Seeger-Weibel, B. Berod, K. Schaer, R. Gamboni, S. Chen, W. Chen, C.T. Jagoe, F.R. Kinder Jr., M. Loo, K. Prasad, O. Repic, W.-C. Shieh, R.-M. Wang, L. Waykole, D.D. Xu, and S. Xue Org. Process Res. Dev. 8 2004 92 and following papers
6. M.A. Burlingame, S.J. Shaw, K.F. Sundermann, D. Zhang, J. Petryka, E. Mendoza, F. Lui, D.C. Myles, M.J. LaMarche, T. Hirose, B.S. Freeze, and A.B. Smith III Bioorg. Med. Chem. Lett. 14 2004 2335
7. D.P. Curran, and T. Furukawa Org. Lett. 4 2002 2233
8. N. Choy, Y. Shin, P.Q. Nguyen, D.P. Curran, R. Balachandran, C. Madiraju, and B.W. Day J. Med. Chem. 46 2003 2846
9. S.J. Shaw, K.F. Sundermann, M.A. Burlingame, D.C. Myles, B.S. Freeze, M. Xian, I. Brouard, and A.B. Smith III J. Am. Chem. Soc. 127 2005 6532
10. A.B. Smith III, and M. Xian Org. Lett. 6 2005 5229
11. Palmero, M. G.; Bair, K. W.; Chen, W.; Guo, Q.; Lassota, P. T.; Sorrensen, E.; Wang, R. M.; Kinder, Jr., F. R., Abstracts of Papers, 224th Meeting of the American Chemical Society, Boston, MA; American Chemical Society: Washington, DC, 2002; Abstract 791.
12. A.B. Smith III, M.D. Kaufman, T.J. Beauchamp, M.J. LaMarche, and H. Arimoto Org. Lett. 1 1999 1823
13. A.B. Smith III, T.J. Beauchamp, M.J. LaMarche, M.D. Kaufman, Y. Qui, H. Arimoto, D.R. Jones, and K. Kobayashi J. Am. Chem. Soc. 122 2000 8654
14. I. Paterson, G.J. Florence, K. Gerlach, J.P. Scott, and N. Sereining J. Am. Chem. Soc. 123 2001 9535
15. L.A. Martello, M.J. LaMarche, L. He, T.J. Beauchamp, A.B. Smith III, and S.B. Horwitz Chem. Biol. 8 2001 843
16. S.P. Gunasekera, R.E. Longley, and R.A. Insbrucker J. Nat. Prod. 64 2001 171
17. Y. Ding, J. Wang, K.A. Abboud, Y. Xu, W.R. Dolbier Jr., and N.G.J. Richards J. Org. Chem. 66 2001 6381
18. Kinder, F. R.; Bair, K., W.; Chen, W.; Florence, G. L.; Francavilla, C.; Geng, P.; Gunerasekera, S.; Lassota, P. T.; Longley, R.; Palermo, M.; Paterson, I.; Pomponi, S.; Ramsey, T. M.; Rogers, L.; Sabio, M.; Sereinig, N.; Sorensen, E.; Wang, R.; Wright, A. 93rd Annual Meeting, San Francisco, CA; American Association for Cancer Research, 2002; Poster 3650.
19. We speculate that the discodermolide methyl ester cyclises to discodermolide in the assay but the 3-deoxy compound does not.