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2. For reviews see: Slichenmyer, W. J.; von Hoff, D. D. J. Clin. Pharmacology 1990, 30, 770; In Taxane Anicancer Agents ACS Symposium Series 583; Georg, G. I.; Chen, T. T.; Ojima, I.; Vyas, D.M., American Chemical Society: Washington, DC 1995.
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note
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3. In 1992 PT was approved by the FDA for the treatment of drug refractory metastatic ovarian cancer.
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5. (a) Nicolaou, K. C.; Yang, Z.; Liu, J. J.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen E. J. Nature 1994, 367, 630; Nicolaou, K. C.; Ueno, H.; Couladouros, E. A. J. Am. Chem. Soc. 1995, 117, 624; Nicolaou, K. C.; Guy, R. K. Angew. Chem. 1995, 107, 2247;
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Claiborne, C.F.7
Renaud, J.8
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0028810338
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5. (a) Nicolaou, K. C.; Yang, Z.; Liu, J. J.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen E. J. Nature 1994, 367, 630; Nicolaou, K. C.; Ueno, H.; Couladouros, E. A. J. Am. Chem. Soc. 1995, 117, 624; Nicolaou, K. C.; Guy, R. K. Angew. Chem. 1995, 107, 2247;
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5. (a) Nicolaou, K. C.; Yang, Z.; Liu, J. J.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen E. J. Nature 1994, 367, 630; Nicolaou, K. C.; Ueno, H.; Couladouros, E. A. J. Am. Chem. Soc. 1995, 117, 624; Nicolaou, K. C.; Guy, R. K. Angew. Chem. 1995, 107, 2247;
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6. Three new classes of natural products with microtubule stabilizing properties have been described in the meantime: (a) the macrolides epothilone A and B: Kowalski, R. J.; Giannakakon, P.; Hamel, E. J. Biological Chem. 1997, 272, 2534; Bollag, D. M.; McQueney, P. A.; Zhu, J.; Hensens, O.; Konpal, L.; Liesch, M. Goetz, E. Lazarides, C.M. Woods Cancer Res. 1995, 55, 2325-2333;
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6. Three new classes of natural products with microtubule stabilizing properties have been described in the meantime: (a) the macrolides epothilone A and B: Kowalski, R. J.; Giannakakon, P.; Hamel, E. J. Biological Chem. 1997, 272, 2534; Bollag, D. M.; McQueney, P. A.; Zhu, J.; Hensens, O.; Konpal, L.; Liesch, M. Goetz, E. Lazarides, C.M. Woods Cancer Res. 1995, 55, 2325-2333;
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Liesch, M.6
Goetz, E.7
Lazarides, C.M.8
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14
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0030039669
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(b) discodermolide: E. ter Haar, J.; Kowalski, R. J.; Hamel, E.; Lin C. M.; Longley, R. E.; Gunasehera, S. P.; Rosenkranz, H. S.; Day, B.W. Biochemistry 1996, 35, 243; and
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Rosenkranz, H.S.7
Day, B.W.8
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15
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0030984058
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(c) eleutherobin: Lindel, T.; Jensen, P. R.; Fenical, W.; Long, B. H.; Casazza, A. M.; Carboni J.; Fairchild, C. R. J. Am. Chem. Soc. 1997, 119, 8744.
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0001635506
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7. Wender, P. A.; Mucciaro, T. P. J. Am. Chem. Soc. 1992, 114, 5878; for further studies in the pinene series see: Wender, P. A.; Glass, T. E. Synlett 1995, 516; Wender, P. A.; Floreancig, P. E.; Glass, T. E.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C. Tetrahedron Lett. 1995, 36, 4939; Wender, P. A.; Glass, T. E.; Krauss, N. E.; Mühlebach, M.; Peschke, B.; Rawlins, D. B. J. Org. Chem. 1996, 61, 7662.
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Mucciaro, T.P.2
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0010475488
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7. Wender, P. A.; Mucciaro, T. P. J. Am. Chem. Soc. 1992, 114, 5878; for further studies in the pinene series see: Wender, P. A.; Glass, T. E. Synlett 1995, 516; Wender, P. A.; Floreancig, P. E.; Glass, T. E.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C. Tetrahedron Lett. 1995, 36, 4939; Wender, P. A.; Glass, T. E.; Krauss, N. E.; Mühlebach, M.; Peschke, B.; Rawlins, D. B. J. Org. Chem. 1996, 61, 7662.
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Synlett
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Wender, P.A.1
Glass, T.E.2
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0029065227
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7. Wender, P. A.; Mucciaro, T. P. J. Am. Chem. Soc. 1992, 114, 5878; for further studies in the pinene series see: Wender, P. A.; Glass, T. E. Synlett 1995, 516; Wender, P. A.; Floreancig, P. E.; Glass, T. E.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C. Tetrahedron Lett. 1995, 36, 4939; Wender, P. A.; Glass, T. E.; Krauss, N. E.; Mühlebach, M.; Peschke, B.; Rawlins, D. B. J. Org. Chem. 1996, 61, 7662.
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Wender, P.A.1
Floreancig, P.E.2
Glass, T.E.3
Natchus, M.G.4
Shuker, A.J.5
Sutton, J.C.6
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19
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0029847589
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7. Wender, P. A.; Mucciaro, T. P. J. Am. Chem. Soc. 1992, 114, 5878; for further studies in the pinene series see: Wender, P. A.; Glass, T. E. Synlett 1995, 516; Wender, P. A.; Floreancig, P. E.; Glass, T. E.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C. Tetrahedron Lett. 1995, 36, 4939; Wender, P. A.; Glass, T. E.; Krauss, N. E.; Mühlebach, M.; Peschke, B.; Rawlins, D. B. J. Org. Chem. 1996, 61, 7662.
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Wender, P.A.1
Glass, T.E.2
Krauss, N.E.3
Mühlebach, M.4
Peschke, B.5
Rawlins, D.B.6
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0010474467
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note
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0010432952
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note
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9. The syntheses of the discussed compounds is described in detail in DE 4416374 and DE 19513040.
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22
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0010474292
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note
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10. Calculations utilized the MM3-force field implemented in Alchemy 2000®.
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25
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0010513328
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13. Data were take from internet http://epnws1.ncicrf.gov:2345/dis3d/drugs/figures/125973gifg.html.
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Lee, V.M.-Y.1
Daughenbaugh, R.2
Trijanowski, J.Q.3
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27
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0010432953
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in press
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15. Michaelis, M. L.; Racial, N.; Chen, Y.; Bechtel, M.; Ragan, R.; Hepperle, M.; Liu, Y.; Georg, G. Journal of Neurochemistry 1998, in press.
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Journal of Neurochemistry
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Michaelis, M.L.1
Racial, N.2
Chen, Y.3
Bechtel, M.4
Ragan, R.5
Hepperle, M.6
Liu, Y.7
Georg, G.8
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