Synthesis and biological evaluation of novel macrocyclic paclitaxel analogues

Organic Letters

Volumn 3, Issue 16, 2001, Pages 2461-2464

  Metaferia, Belhu B ^a   Hoch, Jeannine ^a   Glass, Thomas E ^a   Bane, Susan L ^b   Chatterjee, Sabarni K ^b   Snyder, James P ^c   Lakdawala, Ami ^c   Cornett, Ben ^c   Kingston, David G I ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b BINGHAMTON UNIVERSITY   (United States)

^c EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PACLITAXEL; TUBULIN;

ARTICLE; BINDING SITE; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYCLIZATION; HUMAN; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HUMANS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PACLITAXEL; TUBULIN; TUMOR CELLS, CULTURED;

EID: 0035833713     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016124d     Document Type: Article

References (28)

1. Thayer, A. M. Chem. Eng. News 2000, 78 (45, November 6), 20-21.
2. Schiff, P. B.; Fant, J.; Horwitz, S. B. Nature 1979, 277, 665-667.
3. Nogales, E.; Wolf, S. G.; Downing, K. H. Nature 1998, 391, 199-202.
4. Li, Y.; Poliks, B.; Cegelski, L.; Poliks, M.; Gryczynski, Z.; Piszczek, G.; Jagtap, P. G.; Studelska, D. R.; Kingston, D. G. I.; Schaefer, J.; Bane, S. Biochemistry 2000, 39, 281-291.
5. Rao, S.; He, L.; Chakravarty, S.; Ojima, I.; Orr, G. A.; Horwitz, S. B. J. Biol. Chem. 1999, 274, 37990-37994.
6. Giannakakou, P.; Gussio, R.; Nogales, E.; Downing, K. H.; Zaharevitz, D.; Bollbuck, B.; Poy, G.; Sackett, D.; Nicolaou, K. C.; Fojo, T. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 2904-2909.
7. Gueritte-Voegelein, F.; Guenard, D.; Mangatal, L.; Potier, P.; Guilhem, J.; Cesariao, M.; Pascard, C. Acta Crystallogr. 1990, C46, 781-784.
8. Snyder, J. P.; Nettles, J. H.; Cornett, B.; Downing, K. H.; Nogales, E. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 5312-5316.
9. Barboni, L.; Lambertucci, C.; Appendino, G.; Vander Velde, D. G.; Himes, R. H.; Bombardelli, E.; Wang, M.; Snyder, J. P. J. Med. Chem. 2001, 44, 1576-1587.
10. Boge, T. C.; Wu, Z.-J.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. Bioorg. Med. Chem. Left. 1999, 9, 3047-3052.
11. Ojima, I.; Chakravarty, S.; Tadashi, I.; Lin, S.; He, L.; Horwitz, S. B.; Kuduk, S. B.; Danishefsky, S. J. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4256-4261.
12. Ojima, I.; Lin, S.; Inoue, T.; Miller, M. L.; Borella, C. P.; Geng, X.; Walsh, J. J. J. Am. Chem. Soc. 2000, 122, 5343-5353.
13. For a recent review on RCM, see: Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
14. Staudinger, H. Justus Liebigs Ann. Chem. 1907, 356, 51.
15. Brieva, R.; Crich, J. Z.; Sih, C. J. J. Org. Chem. 1993, 58, 1068-1075.
16. Chen, S.-H.; Kadow, J. F.; Farina, V. J. Org. Chem. 1994, 59, 6156-6158.
17. Holton, R. A.; Zhang, Z.; Clarke, P. A.; Nadizadeh, H.; Procter, D. J. Tetrahedron Lett. 1998, 39, 2883-2886.
18. Holton, R. A.; Biediger, R. J.; Boatman, P. D. In Taxoi®: Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995; pp 97-121.
19. Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y. H.; Sun, C. M.; Brigaud, T. Tetrahedron 1992, 48, 6985-7012.
20. Georg, G. I.; Boge, T. C.; Cheruvallath, Z. S.; Clowers, J. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. In Taxol®: Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995; pp 317-375.
21. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liscamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-449; cf. http://www.schrodinger.com/ macromodel2.html.
22. Nevins, N.; Cicero, D.; Snyder, J. P. J. Org. Chem. 1999, 64, 3979-3986.
23. Snyder, J. P.; Nevins, N.; Cicero, D. O.; Jansen, J. J. Am. Chem. Soc. 2000, 122, 724-725.
24. Ewing, T. J. A.; Kuntz, E. D. J. Comput. Chem. 1997, 18, 1175-1189; cf. http://www.cmpharm.ucsf.edu/kuntz/kuntz.html.
25. Wang, M.; Cornett, B.; Nettles, J.; Liotta, D. C.; Snyder, J. P. J. Org. Chem. 2000, 65, 1059-1068.
26. Dubois, J.; Thoret, S.; Guénard, D.; Guéritte, F. Tetrahedron Lett. 2000, 65, 1059-1068.
27. Kingston, D. G. I.; Chaudhary, A. G.; Chordia, M. D.; Gharpure, M.; Gunatilaka, A. A. L.; Higgs, P. I.; Rimoldi, J. M.; Samala, L.; Jagtap, P. G.; Giannakakou, P.; Jiang, Y. Q.; Lin. C. M.; Hamel, E.; Long, B. H.; Fairchild, C. R.; Johnston, K. A. J. Med. Chem. 1998, 41, 3715-3726.
28. Wang, M.; Snyder, J. P. Unpublished.