Antineoplastic agents. 379. Synthesis of phenstatin phosphate

Journal of Medicinal Chemistry

Volumn 41, Issue 10, 1998, Pages 1688-1695

  Pettit, George R ^a   Toki, Brian ^a   Herald, Delbert L ^a   Verdier Pinard, Pascal ^a   Boyd, Michael R ^a   Hamel, Ernest ^a   Pettit, Robin K ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; COMBRESTATIN A 4; PHENSTATIN; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BACTERIAL GROWTH; CATTLE; DRUG CONFORMATION; DRUG EFFECT; DRUG SYNTHESIS; GROWTH INHIBITION; MICROTUBULE ASSEMBLY; NEISSERIA GONORRHOEAE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BENZOPHENONES; CATTLE; CELL DIVISION; COLCHICINE; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; LEUKEMIA P388; MACROMOLECULAR SUBSTANCES; MOLECULAR STRUCTURE; NEISSERIA GONORRHOEAE; PHOSPHORIC ACID ESTERS; PRODRUGS; PROTEIN BINDING; TUBULIN; TUMOR CELLS, CULTURED;

EID: 0032492959     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970644q     Document Type: Article

References (53)

1. (a) For contribution 378, see: Pettit, G. R.; Bond, T. J.; Herald, D. L.; Penny, M. G.; Doubek, D. L.; Williams, M. D.; Tackett, L. P.; Hooper, J. N. A. Isolation and Structure of Spongilipid from the Republic of Singapore Marine Poriferan Spongia cf. Hispida. Can. J. Chem. 1997, 75, 920-925.
2. (b) Laboratory of Drug Discovery Research and Development, Developmental Therapeutics Program, Division of Cancer Treatment, Diagnosis and Centers, National Cancer Institute, Frederick Cancer Research Development Center, Frederick, MD 21702-1201.
3. (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.
4. (b) Hamel, E. Antimitotic Natural Products and Their Interactions with Tubulin. Med. Res. Rev. 1996, 16, 207-231.
5. (a) Bedford, S. B.; Quarterman, C. P.; Rathbone, D. L.; Slack, J. A.; Griffin, R. J.; Stevens, M. F. G. Synthesis of Water-Soluble Prodrugs of the Cytotoxic Agent Combretastatin A-4. BioMed. Chem. Lett. 1996, 6, 157-160.
6. (b) Medarde, M.; Pelaez-Lamamié de Clairac, R.; Ramos, A. C.; Caballero, E.; López, J. L.; Grávalos, D. G.; San Feliciano, A. Synthesis and Pharmacological Activity of Combretastatin Analogues, Naphthylcombretastatins and Related Compounds. BioMed. Chem. Lett. 1995,5, 229-232.
7. (c) Li, L.; Wang, H.-K.; Kuo, S.-C.; Wu, T.-S.; Mauger, A.; Lin, C. M.; Hamel, E.; Lee, K.-H. Antitumour Agents 155. Synthesis and Biological Evaluation of 3′ ,6,7-Substituted 2-Phenyl-4-quinoIones as Antimicrotubule Agents. J. Med. Chem. 1994, 37, 3400-3407.
8. (d) Mannila, E.; Talvitie, A. Combretastatin Analogues via Hydration of Stilbene Derivatives. Liebigs Ann. Chem. 1993, 1037-1039.
9. (e) Cushman, M.; He, H.-M.; Lin, C. M.; Hamel, E. Synthesis and Evaluation of a Series of Benzylaniline Hydrochlorides as Potential Cytotoxic and Antimitotic Agents Acting by Inhibition of Tubulin Polymerization. J. Med. Chem. 1993, 36, 2817-2821.
10. (f) Cushman, M.; Nagarathnam, D.; Gopal, D.; He, H.-M.; Lin, C. M.; Hamel, E. Synthesis and Evaluation of Analogues of (Z)-l-(4-Methoxyphenyl)-2-(3,4,5-trimethoxyphenylDethene as Potential Cytotoxic and Antimitotic Agents. J. Med. Chem. 1992, 35, 2293-2306.
11. (g) Getahun, Z.; Jurd, L.; Chu, P. S.; Lin, C. M.; Hamel, E. Synthesis of Alkoxy-Substituted Diaryl Compounds and Correlation of Ring Separation with Inhibition of Tubulin Polymerization: Differential Enhancement of Inhibitory Effects under Suboptimal Polymerization Reaction Conditions. J. Med. Chem. 1992, 35, 1058-1067.
12. (h) Cushman, M.; Nagarathnam, D.; Gopal, D.; Chakraborti, A. K.; Lin, C. M.; Hamel, E. Synthesis and Evaluation of Stilbene and Dihydrostilbene Derivatives as Potential Anticancer Agents That Inhibit Tubulin Polymerization. J. Med. Chem. 1991, 34, 2579-2588.
13. (i) Couladouros, E. A.; Soufli, I. C. Total Synthesis of Natural (-)-VCombretastatin D-l. Tetrahedron Lett. 1995, 51, 9369-9372.
14. (a) Kitanaka, S.; Takido, M.; Mizoue, K.; Kondo, H.; Nakaike, S. Oligomeric Stilbenes from Caragana chamlagu LAMARK Root. Chem. Pharm. Bull. 1996, 44, 565-567.
15. (b) Ruby, A. J.; Kuttan, G.; Dinesh Babu, K.; Rajasekharan, K. N.; Kuttan, R. Anti-tumour and Antioxidant Activity of Natural Curcuminoids. Cancer Lett. 1995, 94, 79-83.
16. Pietikainen, P. Asymmetric Epoxidation of Unfunctionalized Alkenes with Periodates Catalyzed by Chiral (Salen) Mn (III) Complexes. Tetrahedron Lett. 1995, 36, 319-322.
17. (a) Popisil, P. J.; Garstem, D. H.; Jacobsen, E. N. X-Ray Structural Studies of Highly Enantioselective Mn(salen) Epoxidation Catalysts. Chem. Eur. J. 1996, 2, 974-980.
18. (b) Palucki, M.; Popisil, P. J.; Zhang, W.; Jacobsen, E. N. Highly Enantioselective, Low-Temperature Epoxidation of Styrene. J. Am. Chem. Soc. 1994, 116, 9333-9334.
19. (c) Quan, R. W.; Li, Z.; Jacobsen, E. N. Enantiofacially Selective Binding of Prochiral Olefins to a Chiral Catalyst via Simultaneous Face-Face and Edge-Face Aromatic Interactions. J. Am. Chem. Soc. 1996, 118, 8156-8157.
20. (d) Brandes, B. D.; Jacobsen, E. N. Highly Enantioselective, Catalytic Epoxidation of Trisubstituted Olefins. J. Org. Chem. 1994, 59, 4378-4380.
21. (e) Chang, S.; Heid, R. M.; Jacobsen, E. N. Enantioselective Epoxidation of Cyclic 1,3-Dienes Catalyzed by a Sterically and Electronically Optimized (Salen) Mn Complex. Tetrahedron Lett. 1994,35, 669-672.
22. (f) Chang, S.; Galvin, J. M.; Jacobsen, E. N. Effect of Chiral Quaternary Ammonium Salts on (salen) Mn-Catalyzed Epoxidation of cis-Olefins. A Highly Enantioselective, Catalytic Route to Trans-Epoxides. J. Am. Chem. Soc. 1994, 116, 6937-6938.
23. (g) Jacobsen, E. N.; Deng, L.; Furukawa, Y.; Martinez, L. E. Enantioselective Catalytic Epoxidation of Cinnamate Esters. Tetrahedron 1994, 50, 4323-4334.
24. 4 Methyl Ester. J. Org. Chem. 1993, 55, 6939-6941.
25. (i) Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. A Practical Method for the Large-Scale Preparation of [N,N′AT-Bis(3,5-di-tert-butylsalicylidene)-l,2-cyclohexanediaminato(2-)] manganese(III) Chloride, a Highly Enantioselective Epoxidation Catalyst. J. Org. Chem. 1994,59, 1939-1942.
26. (j) Yamada, T.; Imagawa, K.; Nagata, T.; Mukaiyama, T. Enantioselective Epoxidation of Unfunctionalized Olefins with Molecular Oxygen and Aldehyde Catalyzed by Optically Active Manganese(III) Complexes. Chem. Lett. 1992, 2231-2234.
27. (k) Takai, T.; Hata, E.; Yorozu, K.; Mukaiyama, T. Cobalt(II) Complex Catalyzed Epoxidation of Olefins by Conbined Use of Molecular Oxygen and Cyclic Ketones. Chem. Lett. 1992, 2077-2080.
28. (1) Irie, R.; Ito, Y.; Katsuki, T. Catalytic epoxidation with Molecular Oxygen Using Nickel Complex. Tetrahedron Lett. 1991, 32, 6891-6894.
29. (m) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. Highly Enantioselective Epoxidation Catalysts Derived from 1,2-Diaminocyclohexane. J. Am. Chem. Soc. 1991, 113, 7063-7064.
30. (a) Cope, A. C.; Trumbull, P. A.; Trumbull, E. R. Base-catalyzed Rearrangement of Epoxides. J. Am. Chem. Soc. 1958, 80, 2844-2848.
31. (b) Parker, R. E. Mechanisms of Epoxide Reactions. Chem. Rev. 1959, 59, 737-799.
32. (c) Alper, H.; Des Roches, D.; Durst, T.; Legault, R. Molybdenum Hexacarbonyl Catalyzed Rearrangement of Epoxides. J. Org. Chem. 1976,41, 3611-3613.
33. (d) Bornstein, J.; Joseph, M. A.; Shields, J. E. Solvolyses of 1,1Diphenyl-2-haloethanols and of 1,1-Diphenylethylene Oxide: Thermal Behavior of the Epoxide and Its Reactions with Phenylmagnesium Bromide and with Phenyllithium. J. Org. Chem. 1965, 30, 801-807.
34. (e) Thummel, R. P.; Rickborn, B. Stereochemistry of the Base-Induced Rearrangement of Epoxides to Allylic Alcohols. J. Am. Chem. Soc. 1970, 92, 2064-2067.
35. 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.
36. Jung, M. E.; Yuk-Sun Lam, P.; Mansuri, M. M.; Speltz, L. M. Stereoselective Synthesis of an Analogue of Podophyllotoxin by an Intramolecular Diels-Alder Reaction. J. Org. Chem. 1985, 50, 1087-1105.
37. Pettit, G. R.; Temple, C., Jr.; Narayanan, V. L.; Vanna, R.; Simpson, M. J.; Boyd, M. R.; Rener, G. A.; Bansal, N, Antineoplastic Agents 322. Synthesis of Combretastatin A-4 Prodrugs. Anticancer Drug Des. 1995, 10, 299-309.
38. 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. Experentia 1989, 45, 209-211.
39. 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 Des. 1995, 10, 243-250.
40. 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.
41. Gardner, J. A. F.; MacDonald, B. F.; MacLean, J. The Polyoxyphenols of Western Red Cedar (Thuja Plicata Donn). Can. J. Chem. 1960, 38, 2387-2394.
42. Kasztreiner, E.; Borsey, J.; Vargha, L. Synthesis and Pharmacological Investigation of New Alkoxybenzamides II. Biochem. Pharmacol. 1962, 11, 651-657.
43. Boyd, M. R. Status of the NCI Preclinical Antitumour Drug Discovery Screen. Implications for Selection of New Agents for Clinical Trial. In CANCER: Principles and Practices of Oncology Updates; De Vita, V. T., Jr., Hellman, S., Rosenberg, S. A., Eds.; Lippincott: Philadelphia, 1989; Vol. 10, No. 3, pp 1-12.
44. Boyd, M. R. The Future of New Drug Development. Section I. Introduction to Cancer Therapy. In Current Therapy in Oncology; Niederhuber, J. E., Ed.; B. C. Decker, Inc.: Philadelphia, 1993; pp 11-22.
45. Boyd, M. R.; Paull, K. D.; Rubinstein, L. R. Data Display and Analysis Strategies from NCI Disease-Oriented in Vitro Antitumour Drug Screen. In Cytotoxic Anticancer Drugs: Models and Concepts for Drug Discovery and Development; Valeriote, F. A., Corbett, T., Baker, L., Eds.; Kluwer Academic Publishers: Amsterdam, 1992; pp 11-34.
46. Stinson, S. F.; Alley, M. C.; Kopp, W. C.; Fiebig, H.-H.; Mullendore, L. A.; Pittman, A. F.; Kenney, S.; Keller, J.; Boyd, M. R. Morphological and Immunocytochemical Characteristics of Human Tumor Cell Lines for Use in a Disease-Oriented Anticancer Drug Screen. Anticancer Res. 1992, 12, 1035-1054.
47. Boyd, M. R.; Paull, K. D. Some Practical Considerations and Applications of the NCI in Vitro Drug Discovery Screen. Drug Dev. Res. 1995, 34, 91-109.
48. Weinstein, J. N.; Myers, T. G.; O'Connor, P. M.; Friend, S. H.; Fornance, A. J.; Kohn, K. W.; Fojo, T.; Bates, S. E.; Rubinstein, L. V.; Anderson, N. L.; Buolamwini, J. K.; van Osdol, W. W.; Monks, A. P.; Scudiero, D. A.; Sausville, E. A.; Zaharevitz, D. W.; Bunow, B.; Viswanadhan, V. N.; Johnson, G. S.; Wittes, R. E.; Paul, K. D. An Information-Intensive Approach to the Molecular Pharmacology of Cancer. Science 1997, 275, 343-349.
49. North, A. C.; Phillips, D. C.; Matthews, F. S. A Semiempirical Method of Absorption Correction. Acta Crystallogr. 1968, A24, 351-359.
50. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guigliardi, A.; Mburla, M.; Polidori, G.; Camalli, M. SIR92 - A Program for Automatic Solution of Crystal Structures by Direct Methods; Dipartimento Geomineralogico, University of Bari, Italy.
51. Preparation of Figure 1 was done with SHELXTL-PLUS, G. Sheldrick, Siemens Analytical X-Ray Instruments, Inc., Madison, WI 53719.
52. Hamel, E.; Lin, C. M. Separation of Active Tubulin and Microtubule-Associated Proteins by Ultracentrifugation and Isolation of a Component Causing the Formation of Microtubule Bundles. Biochemistry 1984, 23 (3), 4173-4184.
53. Kang, G.-J.; Getahun, Z.; Muzaffar, A.; Brossi, A.; Hamel, E. W-Acetylcolchinol O-Methyl Ether and Thiocolchicine, Potent Analogues of Colchicine Modified in the C Ring: Evaluation of the Mechanistic Basis for Their Enhanced Biological Properties. J. Biol. Chem. 1990, 265, 10255-10259.