Synthesis, Modeling, and Anti-Tubulin Activity of a D-Seco Paclitaxel Analogue

Organic Letters

Volumn 6, Issue 4, 2004, Pages 461-464

  Barboni, Luciano ^a   Giarlo, Guido ^a   Ricciutelli, Massimo ^a   Ballini, Roberto ^a   Georg, Gunda I ^a   VanderVelde, David G ^b   Himes, Richard H ^c   Wang, Minmin ^d   Lakdawala, Ami ^d   Snyder, James P ^d  

^a UNIVERSITY OF CAMERINO   (Italy)

^b UNIVERSITY OF KANSAS   (United States)

^c UNIVERSITY OF KANSAS   (United States)

^d EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOCETAXEL; PACLITAXEL; PACLITAXEL DERIVATIVE; TAXANE DERIVATIVE; TUBULIN;

ARTICLE; CYTOTOXICITY; DRUG BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MICROTUBULE; MODEL; PREDICTION; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BINDING SITES; HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PACLITAXEL; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP; TAXOIDS; TUBULIN MODULATORS;

EID: 10744225655     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036204c     Document Type: Article

References (20)

1. Wang, M.; Cornett, B.; Nettles, J.; Liotta, D. C.; Snyder, J. P. J. Org. Chem. 2000, 65, 1059-1068.
2. Barboni, L.; Datta, A.; Dutta, D.; Georg, G. I.; Vander Velde, D. G.; Himes, R. H.; Wang, M.; Snyder, J. P. J. Org. Chem. 2001, 66, 3321-3329.
3. Wang, M.; Xia, X.; Kim, Y.; Hwang, D.; Jansen, J. M.; Botta, M.; Liotta, D. C.; Snyder, J. P. Org. Lett. 1999, 1, 43-46.
4. Snyder, J. P.; Nettles, J. H.; Cornett, B.; Downing, K. N.; Nogales, E. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 5312-5316.
5. Dubois, J.; Thoret, S.; Guéritte, F.; Guénard, D. Tetrahedron Lett. 2000, 41, 3331-3334.
6. Dubois, J.; Guéritte, F. Private communucation.
7. Deka, V.; Dubois, J.; Thoret, S.; Guéritte, F.; Guénard, D. Org Lett. 2003, ASAP.
8. Gunatilaka, A. A. L.; Ramdayal, F. D.; Sarragiotto, M. H.; Kingston, D. G. I.; Sackett, D. L.; Hamel, E. J. Org. Chem. 1999, 64, 2694-2703.
9. Pinder, A. R. Synthesis 1980, 425-452.
10. Hutchins, R. O.; Kandasamy, D.; Maryanoff, C. A.; Masilamani, D.; Maryanoff, B. E. J. Org. Chem. 1977, 42, 82-91.
11. Boge, T. C.; Hepperle, M.; Vander Velde, D. G.; Gunn, C. W.; Grunewald, G. L.; Georg, G. I. Bioorg. Med. Chem. Lett. 1999, 9, 3041-3046.
12. (a) Snyder, J. P.; Nevins, N.; Cicero, D. O.; Jansen, J. J. Am. Chem. Soc. 2000, 722, 724-725.
13. (b) Vander Velde, D. G.; Georg, G. I.; Grunewald, G. L.; Gunn, C. W.; Mitscher, L. A. J. Am. Chem. Soc. 1993, 113, 11650-11651.
14. Liu, Y.; Ali, S. Y.; Boge, T. C.; Georg, G. I.; Victory, S.; Zygmunt, J. ; Marquez, R. T.; Himes, R. H. Combi. Chem. High Thr. Scr. 2002, 5, 39-48.
15. Ewing, T. J. A.; Kuntz, E. E. J. Comput. Chem. 1997, 18, 1175-1189; cf. http://www.cmpharm.ucsf.edu/kuntz/kuntz.html.
16. Wang, M.; Xia, X.; Kim, Y.; Hwang, D.; Jansen, J. M.; Botta, M.; Liotta, D. C.; Snyder, J. P. Org. Lett. 1999, 1, 43-46.
17. Wang, M.; Lakdawala, A.; Snyder, J. P. Unpublished results.
18. (a) Vedani, A.; Zbinden, P.; Snyder, J. P.; Greenidge, P. A. J. Am. Chem. Soc. 1995, 117, 4987-4994.
19. (b) Zbinden, P.; Dobler, M.; Folkers, G.; Vedani, A. Quant. Struct.-Act. Relat. 1998, 17, 122-130.
20. He, L.; Jagtap, P. G.; Kingston, D. G.; Shen, H. J.; Orr, G. A.; Horwitz, S. B. Biochemistry 2000, 39, 3972-3978.