Molecules of interest: Podophyllotoxin

Phytochemistry

Volumn 54, Issue 2, 2000, Pages 115-120

  Canel, Camilo ^a   Moraes, Rita M ^b   Dayan, Franck E ^a   Ferreira, Daneel ^b  

^a AGRICULTURAL RESEARCH SERVICE   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Antineoplastic drugs; Aryltetralin lignan; Berberidaceae; Etopophos; Etoposide; P. emodi; Podophyllotoxin; Podophyllum peltatum; Teniposide; Topoisomerase; Tubulin

Indexed keywords

ARYLTETRALIN LIGNAN; DNA TOPOISOMERASE; ETOPOFOS; ETOPOSIDE; PODOPHYLLOTOXIN; TENIPOSIDE; TUBULIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; REVIEW; CHEMISTRY; SYNTHESIS;

PODOPHYLLOTOXIN;

EID: 0034185943     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(00)00094-7     Document Type: Article

References (20)

1. Allevi P., Anastasia M., Ciuffreda P., Bigatti E., Macdonald P. Stereoselective glucosidation of Podophyllum lignans. A new simple synthesis of etoposide. Journal of Organic Chemistry. 58:1993;4175-4178.
2. Andrews R.C., Teague S.J., Meyers A.I. Asymmetric total synthesis of (-)-podophyllotoxin. Journal of the American Chemical Society. 110:1988;7854-7858.
3. Berkowitz D.B., Maeng J.-H., Dantzig A.H., Shepard R.L., Norman B.H. Chemoenzymatic and ring E-modular approach to the (-)-podophyllotoxin skeleton. Synthesis of 3′,4′,5′-tridemethoxy-(-)-podophyllotoxin. Journal of the American Chemical Society. 118:1996;9426-9427.
4. Broomhead A.J., Rahman M.M., Dewick P.M., Jackson D.E., Lucas J.A. Matairesinol as precursor of Podophyllum lignans. Phytochemistry. 30:1991;1489-1492.
5. Bush E.J., Jones D.W. Asymmetric total synthesis of (-)-podophyllotoxin. Journal of the Chemical Society, Perkin Transactions. 1:1995;151-155.
6. Charlton J.L., Koh K. Asymmetric synthesis of (-)-neopodophyllotoxin. Journal of Organic Chemistry. 57:1992;1514-1516.
7. Davin L.B., Wang H.-B., Crowell A.L., Bedgar D.L., Martin D.M., Sarkanen S., Lewis N.G. Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science. 275:1997;362-366.
8. Hainsworth J.D., Greco F.A. Etoposide: twenty years later. Annals of Oncology. 6:1995;325-341.
9. Huang T.-S., Lee C.-C., Chao Y., Shu C.-H., Chen L.-T., Chen L.-L., Chen M.-H., Yuan C.-C., Whang-Peng J. A novel podophyllotoxin-derived compound GL331 is more potent than its congener VP-16 in killing refractory cancer cells. Pharmaceutical Research. 16:1999;997-1002.
10. Imbert F. Discovery of podophyllotoxins. Biochimie. 80:1998;207-222.
11. Jardine I. Podophyllotoxins. Anticancer Agents Based on Natural Product Models. 1980;319-351 Academic, New York.
12. Kende A.S., King M.L., Curran D.P. Total synthesis of (±)-4′-demethyl-4-epipodophyllotoxin by insertion-cyclization. Journal of Organic Chemistry. 46:1981;2826-2828.
13. Klemm L.H., Olson D.R., White D.V. Electroreduction of α,β-unsaturated esters. Part I: A simple synthesis of rac-deoxypicropodophyllotoxin by intramolecular Diels-Alder reaction plus trans addition of hydrogen. Journal of Organic Chemistry. 36:1971;3740-3743.
14. Macdonald D.I., Durst T. A highly stereoselective synthesis of podophyllotoxin and analogues based on an intramolecular Diels-Alder reaction. Journal of Organic Chemistry. 53:1988;3663-3669.
15. Moraes-Cerdeira R.M., Burandt C.L. Jr., Bastos J.K., Nanayakkara N.P.D., McChesney J.D. In vitro propagation of P. peltatum. Planta Medica. 64:1998;42.
16. Schacter L. Etoposide phosphate: what, why, where, and how? Seminars in Oncology. 23:1996;1-7.
17. Stähelin H.F., von Wartburg A. The chemical and biological route from podophyllotoxin glucoside to etoposide. Cancer Research. 51:1991;5-15.
18. Van Speybroeck R., Guo J., Van der Eycken J., Vandewalle M. Enantioselective total synthesis of (-)-epipodophyllotoxin and (-)-podophyllotoxin. Tetrahedron. 47:1991;4675-4682.
19. Ward, R.S., 1992. Synthesis of podophyllotoxin and related compounds. Synthesis. pp. 719-730.
20. Ziegler F.E., Schwartz J.A. Synthetic studies on lignan lactones: aryl dithiane route to (±)-podorhizol and (±)-isopodophyllotoxone and approaches to the stegane skeleton. Journal of Organic Chemistry. 43:1978;985-991.