Syntheses and structure-activity relationships of taxoids derived from 14β-hydroxy-10-deacetylbaccatin III

Journal of Medicinal Chemistry

Volumn 40, Issue 3, 1997, Pages 267-278

  Ojima, Iwao ^a   Slater, John C ^a   Kuduk, Scott D ^a   Takeuchi, Craig S ^a   Gimi, Rayomand H ^a   Sun, Chung Ming ^a   Park, Young Hoon ^a   Pera, Paula ^b   Veith, Jean M ^b   Bernacki, Ralph J ^b  

^a STONY BROOK UNIVERSITY   (United States)

^b ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BACCATIN III; DRUG DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; P-GLYCOPROTEIN; PACLITAXEL; STRUCTURE-ACTIVITY RELATIONSHIP; TAXOIDS; TUMOR CELLS, CULTURED;

EID: 15644364107     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960563e     Document Type: Article

References (35)

1. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. Plant Antitumor Agents. VI. The Isolation and Structure of Taxol, a Novel Antileukemic and Antitumor Agent from Taxus brevifolia. J. Am. Chem. Soc. 1971, 93, 2325-2327.
2. Guéritte-Voegelein, F.; Mangatal, L.; Guénard, D.; Potier, P.; Guilhem, J.; Cesario, M.; Pascard, C. Structure of a Synthetic Taxol Precursor: N-tert-Butoxycarbonyl-10-deacetyl-N-debenzoyltaxol. Acta Crystallogr. 1990, C46, 781-784.
3. Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; American Chemical Society: Washington, DC, 1995.
4. Suffness, M. Taxol: From Discovery to Therapeutic Use. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed.; Academic Press: San Diego, 1993; Vol. 28, Chapter 32, pp 305-314.
5. Suffness, M. Taxol: Science and Applications; CRC Press: New York, 1995.
6. Rowinsky, E. K.; Onetto, N.; Canetta, R. M.; Arbuck, S. G. Taxol: The First of the Taxanes, and Important New Class of Antitumor Agents. Semin. Oncol. 1992, 19, 646-662.
7. Guénard, D.; Guéritte-Vogelein, F.; Potier, P. Taxol and Taxotere: Discovery, Chemistry, and Structure-Activity Relationships. Acc. Chem. Res. 1993, 26, 160-167.
8. Shiff, P. B.; Fant, J.; Horwitz, S. B. Promotion of Microtubule Assembly in vitro by Taxol. Nature 1979, 277, 665-667.
9. Manfredi, J. J.; Horwitz, S. B. Taxol: an Antimitotic Agent with a New Mechanism of Action. Pharmacol. Ther. 1984, 25, 83-125.
10. Ringel, I.; Horwitz, S. B. Studies with RP 56976 (Taxotère): A Semisynthetic Analogue of Taxol. J. Natl. Cancer Inst. 1991, 83, 288-291.
11. Seidman, A. D. Stony Brook Symposium on Taxol and Taxotère; Stony Brook: New York, 1993; May 14-15, Abstracts pp 14-16.
12. Arbuck, S. G.; Blaylock, B. A. Taxol: Clinical Results and Current Issues in Development. In Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995; pp 379-415.
13. Horwitz, S. B. Stony Brook Symposium on Taxol and Taxotère; Stony Brook: New York, 1993; May 14-15, Abstracts pp 23-24.
14. Verweij, J.; Clavel, M.; Chevalier, B. Ann. Oncol. 1994, 5, 495-505.
15. Ojima, I.; Fenoglio, I.; Park, Y. H.; Sun, C.-M.; Appendino, G.; Pera, P.; Bernacki, R. J. Synthesis and Structure-Activity Relationships of Novel Nor-Seco Analogs of Taxol and Taxotère. J. Org. Chem. 1994, 59, 515-517.
16. Ojima, I.; Duclos, O.; Zucco, M.; Bissery, M.-C.; Combeau, C.; Vrignaud, P.; Riou, J. F.; Lavelle, F. Synthesis and Structure-Activity Relationships of New Antitumor Taxoids. Effects of Cyclohexyl Substitution at the C-3′ and/or C-2 of Taxotère (Docetaxel). J. Med. Chem. 1994, 37, 2602-2608.
17. Ojima, I.; Duclos, O.; Kuduk, S. D.; Sun, C.-M.; Slater, J. C.; Lavelle, F.; Veith, J. M.; Bernacki, R. J. Synthesis and Biological Activity of 3′-Alkyl- and 3′-Alkenyl-3′-Dephenyldocetaxels. Bioorg. Med. Chem. Lett. 1994, 4, 2631-2634.
18. Ojima, I.; Fenoglio, I.; Park, Y. H.; Pera, P.; Bernacki, R. J. Synthesis and Biological Activity of 14β-Hydroxydocetaxel. Bioorg. Med. Chem. Lett. 1994, 4, 1571-1576.
19. Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. Structure-Activity Relationships of New Taxoids Derived from 14β-Hydroxy-10-deacetylbaccatin III. J. Med. Chem. 1994, 37, 1408-1410.
20. Ojima, I.; Park, Y. H.; Fenoglio, I.; Duclos, O.; Sun, C.-M.; Kuduk, S. D.; Zucco, M.; Appendino, G.; Pera, P.; Veith, J. M.; Bernacki, R. J.; Bissery, M.-C.; Combeau, C.; Vrignaud, P.; Riou, J. F.; Lavelle, F. Syntheses and Structure-Activity Relationships of New Taxoids. In Taxane Anticancer Agents: Basic Science and Current Status; ACS Symppsoi, Series 583; Georg; G. I., Chen, T. T., Ojima, I, Vyas, D. M., Eds.; American Chemical Society: Washington, DC, 1995; pp 262-275.
21. Ojima, I.; Slater, J. C.; Michaud, E.; Kuduk, S. D.; Bounaud, P.-Y.; Vrignaud, P.; Bissery, M.-C.; Veith, J.; Pera, P.; Bernacki, R. J. Syntheses and Structure-Activity Relationships of the Second Generation Antitumor Taxoids. Exceptional Activity against Drug-Resistant Cancer Cells. J. Med. Chem. 1996, 39, 3889-3896.
22. Appendino, G.; Gariboldi, P.; Gabetta, B.; Pace, R.; Bombardelli, E.; Viterbo, D. 14β-Hydroxy-10-deacetylbaccatin III, a New Taxane from Himalayan Yew (Torus Wallichiana Zucc.). J. Chem. Soc., Perkins Trans. 1 1992, 2925-2929.
23. Ojima, I.; Habus, I.; Zhao, M.; Georg, G. I.; Jayasinghe, R. Efficient and Practical Asymmetric Synthesis of the Taxol C-13 Side Chain, N-Benzoyl-(2R,3S)-3-phenylisoserine, and Its Analogs via Chiral 3-Hydroxyl-4-aryl-β-lactams Through Chiral Ester Enolate - Imine Cyclocondensation. J. Org. Chem. 1991, 56, 1681-1684.
24. Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y. H.; Sun, C.-M.; Brigaud, T. New and Efficient Approaches to the Semisynthesis of Taxol and Its C-13 Side Chain Analogs by Means of β-Lactam Synthon Method. Tetrahedron 1992, 48, 6985-7012.
25. Holton, R. A. Method for Preparation of Taxol. Eur. Pat. Appl. 1990; U.S. Patent 5,175,315, 1992; EP 400,971, 1990; Chem. Abstr. 1990, 114, 164568q.
26. Georg, G. I.; Cheruvallath, Z. S.; Himes, R. H.; Mejillano, M. R.; Burke, C. T. Synthesis of Biologically Active Taxol Analogues with Modified Phenylisoserine Side Chains. J. Med. Chem. 1992, 35, 4230-4237.
27. Ojima, I.; Sun, C.-M.; Zucco, M.; Park, Y. H.; Duclos, O.; Kuduk, S. D. A Highly Efficient Route to Taxotère by the β-Lactam Synthon Method. Tetrahedron Lett. 1993, 34, 4149-4152.
28. Sikic, B. I. Modulation of Multidrug Resistance: At the Threshold. J. Clin. Oncol. 1993, 11, 1629-1635.
29. Ojima, I.; Duclos, D.; Dormán, G.; Simonot, B.; Prestwich, G. D.; Rao, S.; Lerro, K. A.; Horwitz, S. B. A New Paclitaxel Photoaffinity Analog with a 3-(4-benzoylphenyl)propanoyl Probe for Characterization of Drug-Binding Sites on Tubulin and P-Glycoprotein. J. Med. Chem. 1995, 38, 3891-3894.
30. Sharma, A.; Straubinger, R. M.; Ojima, I.; Bernacki, R. J. Antitumor Efficacy of Taxane Liposomes on a Human Ovarian Tumor Xenograft in Nude Athymic Mice. J. Pharm. Sci. 1995, 84, 1400-1404.
31. Georg, G. I.; Cheruvallath, Z. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. An Efficient Semisynthesis of Taxol from (3R,4S)-N-Benzoyl-3-[(t-butyldimethylsilyl)oxy]-4-phenyl-2-azetidinone and 7-(Triethylsilyl)baccatin III. Bioorg. Med. Chem. Lett. 1993, 3, 2467-2470.
32. Georg, G. I.; Harriman, G. C. B.; Hepperle, M. Heteroaromatic Taxol Analogues: The Chemistry and Biological Activities of 3′-Furyl and 3′-Pyridyl Substituted Taxanes. Bioorg. Med. Chem. Lett. 1994, 4, 1381-1384.
33. Kant, J.; Farina, V.; Fairchild, C.; Kadow, J. F.; Langley, D. R.; Long, B. H.; Rose, W. C.; Vyas, D. M. Synthesis and Antitumor Properties of Novel 14-β-Hydroxytaxol and Related Analogues. Bioorg. Med. Chem. Lett. 1994, 1565.
34. Skehan, P.; Streng, R.; Scudierok, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. New Colorimetric Cytotoxicity Assay for Anti-cancer Drug Screening. J. Natl. Cancer Inst. 1990, 82, 1107-1112.
35. Motulsky, H. J.; Ransnas, L. A. Fitting Curves to Data Using Nonlinear Regression: A Practical and Nonmathematical Review. FASEB J. 1987, 1, 365-374.