Antineoplastic agents 389. New syntheses of the combretastatin A-4 prodrug

Anti-Cancer Drug Design

Volumn 13, Issue 3, 1998, Pages 183-191

  Pettit, George R ^a   Rhodes, Monte R ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

Antineoplastic agents; Combretastatin A 4 prodrug; Phosphate esters

Indexed keywords

ANTINEOPLASTIC AGENT; BENZYL DERIVATIVE; CHLOROTRIMETHYLSILANE; COMBRETASTATIN; DIBENZYLCHLOROPHOSPHITE; METHOXIDE SODIUM; PRODRUG; SILANE DERIVATIVE; SODIUM IODIDE; UNCLASSIFIED DRUG;

ANGIOGENESIS; ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG SYNTHESIS; PHOSPHORYLATION; PRIORITY JOURNAL;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORYLATION; PRODRUGS; STILBENES;

EID: 0031980124     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (37)

1. BEDFORD, S B , QUARTERMAN, C.P., RATHBONE, D.L , SLACK, J.A., GRIFFIN, B.J. & STEVENS, M F G (1996). Synthesis of water-soluble prodrugs of the cytotoxic agent combretastatin A-4. Bioorganic & Medicinal Chemistry Letters, 6, 157.
2. BROWN, R T., FOX, B.W, HADFIELD, J A., MCGOWN, A.T., MAYALARP, S P, PETTIT, G.R. & WOODS, J A (1995). Synthesis of water-soluble sugar derivatives of combretastatin A-4. Journal of the Chemical Society, Perkin Transactions I, 577.
3. BUNDGAARD, H (ED) (1985). Design of Prodrugs. Elsevier: New York.
4. CHAO, H -L., BERNATOWICZ, M.S., KLIMAS, C E. & MATSUEDA, G.R. (1993). N,N-Diisopropyl-bis[2-(trimethylsilyl)ethyl]phosphoramidite. An attractive phosphitylating agent compatible with the Fmoc/t-butyl strategy for the synthesis of phosphotyrosine containing peptides. Tetrahedron Letters, 34, 3377.
5. DARK, G.G., HILL, S.A. , PRISE, V.E., TOZER, G M., PETTIT, G R & CHAPLIN, D.J (1997). Combretastatin A-4, an agent that displays potent and selective toxicity toward tumor vasculature. Cancer Research, 57, 1829.
6. EL-ZAYAT, A A.E., DEGEN, D., DRABEK, S., CLARK, G.M , PETTIT, G.R & VON HOFF, D D. (1993) In Vitro evaluation of the antineoplastic activity of combretastatin A-4, a natural product from Combretum caffrum (arid shrub). Anti-Cancer Drugs, 4, 19.
7. FLYNN, G L & LAMB, D.J. (1970). Factors influencing solvolysis of corticosteroid-21-phosphate esters. Journal of Pharmaceutical Sciences, 59, 1433.
8. GOMBOTZ, W.R & PETTIT, D.K. (1995). Biodegradable polymers for protein and peptide drug delivery. Bioconjugate Chemistry, 6, 332.
9. GREENWALD, R.B, GILBERT, C.W, PENDRI, A., CONOVER, C.D , XIA, J. & MARTINEZ, A. (1996). Drug delivery systems: water soluble taxol 2′-poly(ethylene glycol) ester prodrugs - design and in vivo effectiveness. Journal of Medicinal Chemistry, 39, 424.
10. HANESSIAN, S. & GUINDON, Y. (1980). Chemistry of the glycosidic linkage. Direct conversion of glycosides into 1-thioglycosides by the use of [alkyl (or aryl)thio] trimethylsilanes. Carbohydrate Research, 86, C3.
11. HEJCHMAN, E., HAUGWITZ, R.D. & CUSHMAN, M. (1995). Synthesis and cytotoxicity of water-soluble ambrosin prodrug candidates. Journal of Medicinal Chemistry, 38, 3407.
12. HOYE, T.R , CARUSO, A.J., DELLARIA, J.F. & KURTH, M.J. (1982). Two syntheses of dl-apylsistatin. Journal of the American Chemical Society, 104, 6704.
13. IZAWA, T & KATA, K. (1995). Design and synthesis of an antitumor prodrug released by the reaction with sulfhydryl compounds. Bioorganic & Medicinal Chemistry Letters, 5, 593.
14. JUNGHEIM, L.N. & SHEPHERD, T.A. (1994). Design of antitumor prodrugs: substrates for antibody targeted enzymes. Chemical Reviews, 94, 1553.
15. 4-phospho-L-tyrosine-containing peptides. Helvetica Chimica Acta, 74, 1314.
16. LACKEY, K., STERNBACH, D.D., CROOM, D.K., EMERSON, D.L., EVANS, M G., LEITNER, P.L., LUZZIO, M.J., MCINTYRE, G., VUONG, A., YATES, J. & BESTERMAN, J.M (1996). Water soluble inhibitors of topoisomerase I: quaternary salt derivatives of camptothecin. Journal of Medicinal Chemistry, 39, 713.
17. LIN, C.M , HO, H H , PETTIT, G.R &. HAMEL, E. (1989). Antimitotic natural products combretastatin A-4 and combretastatin A-2: studies on the mechanism of their inhibition of the binding of colchicine to tubulin. Biochemistry, 28, 6984.
18. MAMBER, S.W., MIKKILINENI, A.B. PACK, E.J., ROSSER, M.P, WONG, H., UEDA, Y & FORENZA, S. (1995). Tubulin polymerization by paclitaxel (Taxol) phosphate prodrugs after metabolic activation with alkaline phosphatase. The Journal of Pharmacology and Experimental Therapeutics, 374, 877.
19. MANCINI, M L. & HONEK, J F (1982). A convenient synthesis of β-(trimethylsilyl)ethanol. Tetrahedron Letters, 23, 3249.
20. MUKAI, C, HIRAI, S., KIM, I.J , KIDO, M. & HANAOKA, M. (1996). Studies on the total synthesis of antitumor styryllactones: stereoselective total syntheses of (+)-goniofufurone, (+)-goniobutenolide A, and (-)-goniobutenolide B. Tetrahedron, 52, 6547.
21. NICOLAU, K.C., PAVIA, M.R. & SEITZ, S.P. (1982). Carbohydrates in organic synthesis. Synthesis of 16-membered-ring macrolide antibiotics. 5. Total synthesis of O-mycinosyltylonolide: synthesis of key intermediates. Journal of the American Chemical Society, 104, 2027.
22. OLAH, G.A., NARANG, S.C., GUPTA, B.G.B. & MALHOTRA, R. (1979). Synthetic methods and reactions. 62. Transformations with chlorotrimethylsilane/sodium iodide, a convenient in situ iodotrimethylsilane reagent. Journal of Organic Chemistry, 44, 1247.
23. PERICH, J W. & JOHNS, R B. (1987). A new, convenient and efficient general procedure for the conversion of alcohols into their dibenzyl phosphorotriesters using N,N-diethyl dibenzyl phosphoramidite. Tetrahedron Letters, 28, 101.
24. PERICH, J E. & JOHNS, R.B (1988). Di-tert-butyl-N,N-diethylphosphoramidite. A new phosphitylating agent for the efficient phosphorylation of alcohols. Synthesis, 142.
25. PETTIT, G.R , SINGH, S.B., HAMEL, E., LIN, C M., ALBERTS, D S & GARCIA-KENDAL, D. (1989). Isolation and structure of the strong cell-growth and tubulin inhibitor combretasiatin A-4. Experientia, 45, 209.
26. PETTIT, G.R., FREEMAN, S., SIMPSON, M.J., THOMPSON, M.A., BOYD, M.R., WILLIAMS, M.D , PETTIT, G.R. III & DOUBEK, D.L (1995a). Antineoplastic agents 320: synthesis of a practical pancratistatin prodrug. Anti-Cancer Drug Design, 10, 243.
27. PETTIT, G.R., TEMPLE, C JR, NARAYANAN, V L , VARMA, R., SIMPSON, M J, BOYD, M R., RENER, G.A. & BANSAL, N (1995b). Antineoplastic agents 322. Synthesis of combretastatin A-4 prodrugs. Anti-Cancer Drug Design, 10, 299.
28. PETTIT, G R , SINGH, S.B., BOYD, M.R., HAMEL, E., PETTIT, R K., SCHMIDT, J.M. & HOGAN, F. (1995c). Antineoplastic agents 291. Isolation and synthesis of combretastatin A-4, A-5, and A-6. Journal of Medicinal Chemistry, 38, 1666.
29. PIOTTO, M E , GRANGER, J.N., CHO, Y., FARSCHTSCHI, N. & GORENSTEIN, D.G. (1991). Synthesis, NMR and structure of oligonucleotide phosphorodithioates. Tetrahedron, 47, 2449.
30. ROEMER, S., RUDOLF, M.T., STADLER, C. & SCHULTZ, C, (1995). Synthesis of D-myo-inositol 3,4,5,6- and 1,4,5,6-tetrakisphosphate analogues and their membrane-permeant derivatives. Journal of the Chemical Society, Chemical Communications, 411.
31. SAULNIER, M.G., LANGLEY, D.R., KADOW, J.F, SENTER, P.D., KNIPE, J.O., TUN, M.M., VYAS, D.M. & DOYLE, T.W. (1994). Synthesis of etoposide phosphate, BMY-40481: a water-soluble clinically active prodrug of etoposide. Bioorganic & Medicinal Chemistry Letters, 4, 2567.
32. SILVERBERG, L.J., DILLON, J.L. & VEMISHETTI, P. (1996). A simple, rapid and efficient protocol for the selective phosphorylation of phenols with dibenzyl phosphite. Tetrahedron Letters, 37, 771.
33. THOMSON, W., NICHOLLS, D , IRWIN, W.J., AL-MUSHADANI, J.S., FREEMAN, S., KARPAS, A , PETRIK, J., MAHMOOD, N & HAY, A.J. (1993). Synthesis, bioactivation and anti-HIV activity of the bis(4-acyloxybenzyl) and mono(4-acyloxybenzyl) esters of the 5′-monophosphate of AZT. Journal of the Chemical Society, Perkin Transactions I, 1239.
34. UEDA, Y., MIKKILINENI, A.B , KNIPE, J.O., ROSE, WC., CASAZZA, A.M & VYAS, D.M. (1993). Novel water soluble phosphate prodrugs of Taxol possessing in vivo antitumor activity. Bioorganic & Medicinal Chemistry Letters, 3, 1761.
35. UEDA, Y., MATISKELLA, J.D , MIKKILINENI, A.B , FARINA, V., KNIPE, J O., ROSE, WC, CASAZZA, A.M. & VYAS, D.M. (1995). Novel, water-soluble phosphate derivatives of 2′-ethoxy carbonylpaclitaxel as potential prodrugs of paclitaxel: synthesis and antitumor evaluation. Bioorganic & Medicinal Chemistry Letters, 5, 247.
36. VARMA, R.S., CHATTERJEE, A K. & VARMA, M. (1993). Alumina-mediated microwave thermolysis: a new approach to deprotection of benzyl esters. Tetrahedron Letters, 34, 4603.
37. WOODS, J.A., HADFIELD, J.A., PETTIT, G.R , FOX, B.W. & MCGOWN, A.T. (1995). The interaction with tubulin of a series of stilbenes based on combretastatin A-4. British Journal of Cancer, 71, 705.