Conformationally restricted paclitaxel analogues: Macrocyclic mimics of the 'hydrophobic collapse' conformation

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 20, 1999, Pages 3047-3052

  Boge, Thomas C ^a   Wu, Zhi Jun ^a   Himes, Richard H ^a   Vander Velde, David G ^a   Georg, Gunda I ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID; DRUG ANALOG; MACROCYCLIC COMPOUND; PACLITAXEL; PHENYL GROUP;

ARTICLE; BINDING AFFINITY; CHEMICAL MODIFICATION; CONFORMATION; HYDROPHOBICITY; MICROTUBULE ASSEMBLY; PARTIAL DRUG SYNTHESIS; STRUCTURE ANALYSIS;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; MOLECULAR CONFORMATION; PACLITAXEL;

EID: 0033581642     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00522-3     Document Type: Article

References (19)

1. Present address: University of Missouri-Kansas City, Division of Pharmaceutical Sciences, Kansas City, MO 64110-2499.
2. Present address: Coelacanth Corp., 100 Jersey Avenue Building A-103, New Brunswick, NJ 08901.
3. For review: Holmes, F. A.; Kudelka, A. P.; Kavanagh, J. J.; Huber, M. H.; Ajani, J. A.; Valero, V. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; American Chemical Society: Washington D. C., 1995; Vol. ACS Symposium Series 583, p 31.
4. Vander Velde, D. G.; Georg, G. I.; Grunewald, G. L.; Gunn, K.; Mitscher, L. A. J. Am. Chem. Soc. 1993, 115, 11650.
5. Paloma, L. G.; Guy, R. K.; Wrasidlo, W.; Nicolaou, K. C. Chem. Biol 1994, 1, 107.
6. Mastropaolo, D.; Camerman, A.; Luo, Y.; Brayer, G. D.; Camerman, N. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6920.
7. Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664.
8. Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337.
9. For review: 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: Boca Raton, FL, 1995, p 317.
10. 3. For example, see: Wang, M.; Xia, X.; Kim, Y.; Hwang, D.; Jansen, J. M.; Botta, M.; Liotta, D. C.; Snyder, J. P. Org. Lett. 1999, 1, 43, and references cited therein.
11. Hart, D. J.; Kanai, K.; Thomas, D. G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289.
12. Georg, G. I.; Cheruvallath, Z. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. Bioorg. Med. Chem. Lett. 1993, 3, 2467.
13. The enantiomeric excess was determined by HPLC on a chiral column. For details of the HPLC analysis see reference 7.
14. Georg, G. I.; Cheruvallath, Z. S.; Harriman, G. C. B.; Hepperle, M.; Park, H.; Himes, R. H. Bioorg. Med. Chem. Lett. 1994, 4, 2331.
15. Georg, G. I.; Ali, S. M.; Boge, T. C.; Datta, A.; Falborg, L.; Park, H.; Mejillano, M.; Himes, R. H. Bioorg. Med. Chem. Lett. 1995, 5, 259.
16. 50 refers to the concentration that produces 50% inhibition of proliferation after 40h incubation.
17. Ojima, I.; Chakravarta, S.; Inoue, T.; Lin, S.; He, L.; Horwitz, S. B.; Danishefsky, S. J. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4256.
18. Nogales, E.; Wolf, S. G.; Downing, K. Nature, (London) 1998, 391, 199.
19. Snyder, J. P.; Cornett, B.; Downing, K.; Nogales, E. 1999. (Submitted for publication.) We thank Professor Snyder and collaborators for informing us of their results prior to publication.