Isoapoptolidin: Structure and Activity of the Ring-Expanded Isomer of Apoptolidin

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3819-3822

  Wender, Paul A ^a   Gulledge, Aaron V ^a   Jankowski, Orion D ^a   Seto, Haruo ^b  

^a STANFORD UNIVERSITY   (United States)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; APOPTOLIDIN; MACROLIDE; PROTON TRANSPORTING ADENOSINE TRIPHOSPHATE SYNTHASE;

ARTICLE; CHEMISTRY; CONFORMATION; DRUG ANTAGONISM; IC 50; ISOMERISM; KINETICS; SOLUBILITY; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; INHIBITORY CONCENTRATION 50; ISOMERISM; KINETICS; MACROLIDES; MITOCHONDRIAL PROTON-TRANSLOCATING ATPASES; MOLECULAR CONFORMATION; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0013072405     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0266222     Document Type: Article

References (22)

1. (a) Kim, J. W.; Adachi, H.; Shin-ya, K.; Hayakawa, Y.; Seto, H. J. Antibiotics 1997, 50, 628.
2. (b) Hayakawa, Y.; Kim, J. W.; Adachi, H.; Shin-ya, K.; Fujita, K.; Seto, H. J. Am. Chem. Soc. 1998, 120, 3524.
3. Developmental Therapeutics Program NCI/NIH. http://dtp.nci.nih.gov (accessed July 2002).
4. (a) Salomon, A. R.; Voehringer, D. W.; Herzenberg, L. A.; Khosla, C. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 14766.
5. (b) Salomon, A. R.; Voehringer, D. W.; Herzenberg, L. A.; Khosla, C. Chem. Biol. 2001, 8, 71.
6. (c) Salomon, A. R.; Zhang, Y.; Seto, H.; Khosla, C. Org. Lett. 2001, 3, 57.
7. (a) Schuppan, J.; Wehlan, H.; Keiper, S.; Koert, U. Angew. Chem., Int. Ed. 2001, 40, 2063.
8. (b) Schuppan, J.; Ziemer, B.; Koert, U. Tetrahedron Lett. 2000. 41, 621.
9. (c) Toshima, K.; Arita, T.; Kato, K.; Tanaka, D.; Matsumura, S. Tetrahedron Lett. 2001, 42, 8873.
10. (d) Nicolaou, K. C.; Li, Y.; Fylaktakidou, K. C.; Mitchell, H. J.; Wei, H. X.; Weyershausen, B. Angew. Chem., Int. Ed. 2001, 40, 3849.
11. (e) Nicolaou, K. C.; Li, Y.; Fylaktakidou, K. C.; Mitchell, H. J.; Sugita, K. Angew. Chem., Int. Ed. 2001, 40, 3854.
12. (f) Nicolaou, K. C.; Li, Y.; Weyershausen, B.; Wei, H. X. Chem. Commun. 2000, 307.
13. (g) Sulikowski, G. A.; Jin, B. H.; Lee, W. M.; Wu, B. Abstracts of Papers, 218th National Meeting of the American Chemical Society, New Orleans, LA, Aug 22-26, 1999; American Chemical Society: Washington, DC, 1996; 563-ORGN.
14. (h) Sulikowski, G. A.; Jin, B. H.; Lee, W. M.; Wu, B. Org. Lett. 2000, 2, 1439.
15. In a typical procedure, 1.0 g of cell extract was purified using a 40 cm × 2.5 cm flash column of 230-400 mesh normal-phase silica eluting with 7% methanol in chloroform.
16. (a) Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caulfield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
17. (b) Calculations performed using the GB/ SA water solvation model: Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127.
18. Image rendered using VMD-Visual Molecular Dynamics: Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graphics 1996, 14, 33.
19. Dulbecco, R.; Vogt, M. J. Exp. Med. 1957, 106, 167.
20. Baseline separation can be achieved using a 150 × 4.6 mm C18/5 μ column eluting with a water/acetonitrile gradient from 40% to 90% over 30 min.
21. 1 is 10.5 h.
22. Roberts, H.; Choo, W. M.; Murphy, M.; Marzuki, S.; Lukins, H. B.; Linnane, A. W. FEBS Lett. 1979, 108, 501.