Synthesis and antimitotic/cytotoxic activity of hemiasterlin analogues

Journal of Natural Products

Volumn 66, Issue 2, 2003, Pages 183-199

  Nieman, James A ^a   Coleman, John E ^a   Wallace, Debra J ^a   Piers, Edward ^a   Lim, Lynette Y ^a   Roberge, Michel ^a   Andersen, Raymond J ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMITOTIC AGENT; ANTINEOPLASTIC AGENT; HEMIASTERLIN; HEMIASTERLIN DERIVATIVE; N,BETA,BETA TRIMETHYLPHENYLALANYL TERT LEUCYL N METHYL 4 AMINO 2,5 DIMETHYLHEX 2 ENOIC ACID; TALTOBULIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN MCF 7; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG SCREENING ASSAYS, ANTITUMOR; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PORIFERA; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

MINK CELL FOCUS-FORMING VIRUS;

EID: 0037331338     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np020375t     Document Type: Article

References (39)

1. Hamel, E. Med. Res. Rev. 1996, 16, 207-231.
2. (a) Sonnichsen, D. S.; Relling, M. V. Paclitaxel and Docetaxel. In A Clinician's Guide to Chemotherapy Pharmacokinetics and Pharmacodynamics; Growchow, L. B., Ames, M. M., Eds.; Williams and Wilkens: Baltimore, 1998; pp 375-394.
3. (b) Leveque, D.; Jehl, F.; Montreil, H. Vinblastine, Vincristine, and Vinorelbine. In A Clinician's Guide to Chemotherapy Pharmacokinetics and Pharmacodynamics; Williams and Wilkens: Baltimore, 1998; pp 459-470.
4. Allen, S. L.; Villalona-Calero, M.; Jakimowicz, K.; Fram. R.; O'Mara, V.; Kolitz, J. E.;Gallagher, M. A.; Van Echo, D.; Fischkoff, S.; O'Dwyer, P. Proc. Am. Assoc. Cancer Res. 1997, 38, 222.
5. Bagniewski, P. G.; Reid, J. M.; Pitot, H. C.; Sloan, J. A.; Ames, M. M. Proc. Am. Assoc. Cancer Res. 1997, 38, 221-222.
6. Altmann, K.-H. Curr. Opin. Chem. Biol. 2001, 5, 424-431.
7. Britton, R.; de Silva, E. D.; Bigg, C. M.; McHardy, L. M.; Roberge, M.; Andersen, R. J. J. Am. Chem. Soc. 2001, 123, 8632-8633.
8. Talpir, R.; Benayahu, Y.; Kashman, Y.; Pannell, L.; Schleyer, M. Tetrahedron Lett. 1994, 35, 4453-4456.
9. Coleman, J. E.; de Silva, E. D.; Kong, F.; Andersen, R. J.; Allen, T. M. Tetrahedron 1995, 51, 10653-10662.
10. Coleman, J. E.; Patrick, B. O.; Andersen, R. J.; Rettig, S, J. Acta Crystallogr. 1996, C52, 1525-1527.
11. Gamble, W. R.; Durso, N. A.; Fuller, R. W.; Westergaard, C. K.; Johnson, T. R.; Sackett,D. L.; Hamel, E.; Cardellina, J. H.; Boyd, M. R. Bioorg. Med. Chem. 1999, 7, 1611-1615.
12. Crews, P.; Farias, J. J.; Emrich, R.; Keifer, P. A. J. Org. Chem. 1994, 59, 2932-2934.
13. Anderson, H. J.; Coleman, J. E.; Andersen, R. J.; Roberge, M. Cancer Chemother. Pharmacol. 1997, 39, 223-226.
14. Bai, R.; Durso, N. A.; Sackett, D. L.; Hamel, E. Biochemistry 1999, 38, 14302-14310.
15. Andersen, R. J.; Coleman, J. E.; Piers, E.; Wallace, D. J. Tetrahedron Lett. 1997, 38, 317-320.
16. (a) Vedejs, E.; Kongkittingam, C. J. Org. Chem. 2001, 66, 7355-7364.
17. (b) Reddy, R.; Jaquith, J. B.; Neelagiri, V. R.; Saleh-Hanna, S.; Durst, T. Org. Lett. 2002, 4, 695-697.
18. The synthesis of SPA110 was first reported in: Andersen, R.; Piers, E.; Nieman, J.; Coleman, J.; Roberge, M. WO Patent 99/32509,1999.
19. (a) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030.
20. (b) Evans, D. A.; Evrard, D. A.; Rychnovsky, S. D.; Früh, T.; Whittingham, W. G.; DeVries, K. M. Tetrahedron Lett. 1992, 33, 1189-1192.
21. Griffith, W. P.; Ley, S. V. Aldrichim. Acta 1990, 23, 13.
22. Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091-2096.
23. Hoffman, A. J. Am. Chem. Soc. 1929, 51, 2542-2547.
24. 3 was prepared by the method of Dermer, O. C.; Edmison, M. T. J. Am. Chem. Soc. 1955, 77, 70-73.
25. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141-6144.
26. Fehrentz, J. A.; Castro, B. Synthesis 1983, 676-678.
27. Roberge, M.; Cinel, B.; Anderson, H. J.; Lim, L.; Jiang, X.; Xu, L.; Kelly, M. T.; Andersen, R. J. Cancer Res. 2000, 60, 5052-5058.
28. Fan, S. J.; Smith, M. L.; Rivet II, D. J.; Duba, D.; Zhan, Q. M.; Kohn, K. W.; Fornace, A. J., Jr.; O'Connor, P. M. Cancer Res. 1995, 55, 1649-1654.
29. (a) SPA110 has been licensed by Wyeth and given the code number HTI-286. The results of the preclinical animal testing on SPA110/ HTI-286 have been the subject of a conference presentation: Loganzo, F.; Discafani, C.; Annable, T.; Beyer, C.; Musto, S.; Hardy, C.; Hernandez, R.; Baxter, M.; Ayral-Kaloustian, S.; Zask, A.; Singanallore, T.; Khafizova, G.; Asselin, A.; Poruchynsky, M. S.; Fojo, T.; Nieman, J.; Andersen, R. J.; Greenberger, L. M. American Association for Cancer Research, Annual Meeting, April 6-10, 2002, San Francisco, CA, and a submitted publication: Loganzo, F.; Discafani, C.; Annable, T.; Beyer, C.; Musto, S.; Tan, X.; Hardy, C.; Hernandez, R.; Baxter, M.; Singanallore, T.; Khafizova, G.; Asselin, A.; Poruchynsky, M. S.; Fojo, T.; Nieman, J. A.; Ayral-Kaloustian, S.; Zask, A.; Andersen, R. J.; Greenberger, L. M. Cancer Res. 2002, July.
30. (a) SPA110 has been licensed by Wyeth and given the code number HTI-286. The results of the preclinical animal testing on SPA110/ HTI-286 have been the subject of a conference presentation: Loganzo, F.; Discafani, C.; Annable, T.; Beyer, C.; Musto, S.; Hardy, C.; Hernandez, R.; Baxter, M.; Ayral-Kaloustian, S.; Zask, A.; Singanallore, T.; Khafizova, G.; Asselin, A.; Poruchynsky, M. S.; Fojo, T.; Nieman, J.; Andersen, R. J.; Greenberger, L. M. American Association for Cancer Research, Annual Meeting, April 6-10, 2002, San Francisco, CA, and a submitted publication: Loganzo, F.; Discafani, C.; Annable, T.; Beyer, C.; Musto, S.; Tan, X.; Hardy, C.; Hernandez, R.; Baxter, M.; Singanallore, T.; Khafizova, G.; Asselin, A.; Poruchynsky, M. S.; Fojo, T.; Nieman, J. A.; Ayral-Kaloustian, S.; Zask, A.; Andersen, R. J.; Greenberger, L. M. Cancer Res. 2002, July.
31. Additional analogues have also been prepared: Zask, A.; Birnberg, B.; Cheung, K.; Cole, D.; Kaplan, J.; Niu, C.; Norton, E.; Sandanayaka, V.; Suayan, R.; Tang, Z.; Yamashita, A.; Loganzo, F.; Beyer, C.; Discafani, C.; Greenberger, L. M.; Ayral-Kaloustian, S. AACR 93rd Annual Meeting April 6-10, 2002 San Francisco, CA.
32. Perrin, D. P.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: Toronto, 1988.
33. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
34. Hagihara, M.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6570-6571.
35. Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6568-6570.
36. Carpino, L. A.; El-Faham, A.; Albericio, F. J. Org. Chem. 1995, 60, 3561-3564, and references therein.
37. PyBOP and PyBroP are described in: Frérot, E. Coste, J.; Pantaloni, A.; Dufour, M.-M.; Jouin, P. Tetrahedron 1991, 47, 259-270.
38. 3, 2,4,6-triisopropylbenzenesulfonyl azide; TsOH, p-toluenesulfonic acid.
39. N-Boc-tert-leucine was purchased from Advanced ChemTech.