Antineoplastic agents. 443. Synthesis of the cancer cell growth inhibitor hydroxyphenstatin and its sodium diphosphate prodrug

Journal of Medicinal Chemistry

Volumn 43, Issue 14, 2000, Pages 2731-2737

  Pettit, George R ^a   Grealish, Matthew P ^a   Herald, Delbert L ^a   Boyd, Michael R ^b   Hamel, Ernest ^b   Pettit, Robin K ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BENZOPHENONE DERIVATIVE; COMBRETASTATIN A1; COMBRETASTATIN A4; HYDROXYPHENSTATIN; PHENSTATIN; PRODRUG; TUBULIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; EXTRACT; HUMAN; HUMAN CELL; LEUKEMIA P 388; OXIDATION; PHOSPHORYLATION; PROTEIN POLYMERIZATION; STRUCTURE ACTIVITY RELATION; TREE;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; BENZOPHENONES; BIOPOLYMERS; COLCHICINE; CRYSTALLOGRAPHY, X-RAY; DIPHOSPHATES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MICE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; TUBULIN; TUMOR CELLS, CULTURED;

EID: 0034644193     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000045a     Document Type: Article

References (33)

1. For contribution 442, see: Pettit, G. R.; Lippert, J. W., III.; Boyd, M. R.; Hamel, E.; Pettit, R. K. Antineoplastic Agents 442. The Remarkable Antitubulin Assembly and Cancer Cell Growth Inhibitor Dioxostatin. J. Med. Chem. Submitted.
2. (a) Morton, J. F. Major Medicinal Plants, C. G. Thomas, Springfield, IL, 1997; p. 87-90.
3. (b) Hartwell, J. L.; Schrecker, A. W. Fortsch. Chem. Org. Nat. 1958, 83.
4. (c) Pettit, G. R. The Scientific Contributions of Jonathan L. Hartwell, Ph.D. J. Nat. Prod. 1995, 58, 359-364.
5. (a) Cragg, G. M.; Newman, D. J. Discovery and development of Antineoplastic Agents from Natural Sources. Cancer Investigation 1999, 17, 153-163.
6. (b) Pettit, G. R.; Alkalay, D. S. Potential Cancerocidal Agents I. The Aromatic System of Podophyllotoxin. (Part A). J. Org. Chem. 1960, 25, 1363-1365.
7. (c) Pettit, G. R.; Baumann, M. F.; Rangammal, K. N. Antineoplastic Agents V. The Aromatic System of Podophyllotoxin (Part B). J. Med. Pharm. Chem. 1962, 5, 800-808.
8. (a) Pettit, G. R.; Singh, S. B.; Boyd, M. R.; Hamel, E.; Pettit, R. K.; Schmidt, J. M.; Hogan, F. Antineoplastic Agents 291. Isolation and Synthesis of Combretastatins A-4, A-5, and A-6. J. Med. Chem. 1995, 38, 1666-1672.
9. (b) Hamel, E. Antimitotic Natural Products and their Interactions with Tubulin. Med. Res. Rev. 1996, 16, 207-231.
10. (c) Pettit, G. R.; Rhodes, M. R.; Herald, D. L.; Chaplin, D. J.; Stratford, M.; Pettit, R. K.; Chapuis, J.-C.; Oliva, D. Antineoplastic Agents 393. Synthesis of the transisomer of Combretastatin A-4 Prodrug. Anti-Cancer Drug Design 1998, 13, 981-994.
11. (d) Pettit, G. R.; Rhodes, M. R. Antineoplastic Agents 389. New Syntheses of the Combretastatin A-4 Prodrug. Anti-Cancer Drug Design 1998, 13, 183-191.
12. Pettit, G. R.; Toki, B.; Herald, D. L.; Verdier-Pinard, P.; Boyd, M. R.; Hamel, E.; Pettit, R. K. Antineoplastic Agents 379. Synthesis of Phenstatin Phosphate. J. Med. Chem. 1998, 41, 1688-1695.
13. Chaplin, D. J.; Pettit, G. R.; Hill, S. A. Antivascular Approaches to Solid Tumor Therapy: Evaluation of Combretastatin A-4 Phosphate. Anticancer Res. 1999, 19, 189-195.
14. Greene, T. W.; Wutz, P. G. M. Protective Groups in Organic Synthesis. J. Wiley & Sons: New York, 1999; pp 27-33.
15. Nahm, S.; Weinreb, S. M. N-Methoxy-N-methylamides as Effective Acylating Agents. Tetrahedron Lett. 1981, 22, 3815-3818.
16. Collins, S.; Hang, Y. Alkyl and Aryllanthanum Triflates: New Reagents for the Conversion of Tertiary Amides to Ketones. Tetrahedron Lett. 1987, 28, 4391-4394.
17. Maeda, H.; Okamoto, J.; Ohmori, H. Reactions of In Situ Formed Acyl Tributylphosphonium Ions with Grignard Reagents as an Effective Route to Ketones from Acid Chlorides. Tetrahedron Lett. 1996, 37, 5381-5384.
18. Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Ronzini, L. Functionalized Ketones by Iron Mediated Reaction of Grignard Reagents with Acyl Chlorides. Tetrahedron Lett. 1987, 28, 2053-2056.
19. Verdier-Pinard, P.; Lai, J.-Y.; Yoo, H.-D.; Yu, J.; Marquez, B.; Nagle, D. G.; Nambu, M.; White, J. D.; Falck, J. R.; Gerwick, W. H.; Day, B. W.; Hamel, E. Structure-activity Analysis of the Interaction of Curacin A, the Potent Colchicine Site Antimitotic Agent, with Tubulin and Effects of Analogues on the Growth of MCF-7 Breast Cancer Cells. Mol. Pharmacol. 1998, 53, 62-76.
20. Pettit, G. R.; Lippert, J. W., III, Herald, D. L.; Pettit, R. K.; Hamel, E. Antineoplastic Agents 440. Asymmetric Synthesis and Evaluation of the Combretastatin A-1 SAR Probes (1S,2S) and (1R,2R)-1,2-Dihydroxy-1-(2′,3′-dihydroxy-4′-methoxyphenyl)-2- (3′,4′,5′-trimethoxyphenyl)-ethane. J. Nat. Prod. In press.
21. Pettit, G. R.; Singh, S. B.; Hamel, E.; Lin, C. M.; Alberts, D. S.; Garcia-Kendall, D. Isolation and Structure of the Strong Cell Growth and Tubulin Inhibitor Combretastatin A-4. Experientia 1989, 45, 209-211.
22. Pettit, G. R.; Freeman, S.; Simpson, M. J.; Thompson, M. A.; Boyd, M. R.; Williams, M. D.; Pettit, G. R. III; Doubek, D. L. Antineoplastic Agents 320. Synthesis of a Practical Pancratistatin Prodrug. Anticancer Drug Design 1995, 10, 243-250.
23. Silverberg, L. J.; Dillon, J. L.; Vemishetti, P. A Simple, Rapid and Efficient Protocol for the Selective Phosphorylation of Phenols with Dibenzyl Phosphite. Tetrahedron Lett. 1996, 37, 771-774.
24. Lambooy, J. P. The Syntheses, Paper Chromatography and Substrate Specificity for Tyrosinase of 2,3-,2,4-,2,5-,2,6-and 3,5-Dihydroxyphenylalanines. J. Am. Chem. Soc. 1954, 76, 133-138.
25. Simig, G.; Schlosser, M. The Synthesis of 6-Methoxy-7,8-methylenedioxyisoquinoline Derivatives. ACH-Models Chem. 1994, 131, 217-228.
26. Brink, M. Bromo Derivatives of o-Vanillin and o-Bourbonal. Chem. Abstr. 1968, 69, 76823.
27. Cleaver, L.; Nimgirawath, S.; Ritchie, E.; Taylor, W. C. The Alkaloids of elmerrilla papuana (Magnoliaceae): Structure and Synthesis of Elmerrillicine. Aust. J. Chem. 1976, 29, 2003-2021.
28. Friedman, D.; Ginsburg, D. Halogenation of Pyrogallol Trimethyl Ether and Similar systems. J. Org. Chem. 1958, 23, 16-17.
29. Harding, V. J. 2-Hydroxy-3:4:3′:4′:5′Pentamethoxybenzophenone and its Derivatives. J. Chem. Soc. 1906, 89, 1665.
30. XPREP-The automatic space group determination program in the SHELXTL. (see ref 25).
31. North, A. C. T.; Phillips, D. C.; Mathews, F. S. A Semiempirical Method of Absorption Correction. Acta Crystallogr. 1968, A2, 351-359.
32. SHELXTL-PC Version 5.1, 1997, an integrated software system for the determination of crystal structures from diffraction data, Bruker Analytical X-ray Systems, Inc., Madison, WI 53719. This package includes, among others: XPREP, an automatic space group determination program; XS, the Bruker SHELXS module for the solution of X-ray crystal structures from diffraction data; XL, the Bruker SHELXL module for structure refinement; XP, the Bruker interactive graphics display module for crystal structures.
33. National Committee for Clinical Laboratory Standards 1997. Performance standards for antimicrobial disk susceptibility tests, 6th ed.; Approved Standard M2-A6. NCCLS: Wayne, PA, 1997.