Preparation and cytotoxicity of podophyllotoxin derivatives lacking the lactone ring

Tetrahedron

Volumn 53, Issue 46, 1997, Pages 15743-15760

  Gordaliza, Marina ^a   Castro, M Angeles ^a   Miguel del Corral, José M ^a   López Vázquez, M Luisa ^a   García, Pablo A ^a   Feliciano, Arturo San ^a   García Grávalos, M Dolores ^b   Broughton, Howard ^c  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b PHARMAMAR S A   (Spain)

^c NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PODOPHYLLOTOXIN DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; COLON CARCINOMA; CONFORMATION; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOLECULAR MODEL; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0030835145     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10042-4     Document Type: Article

References (40)

1. Ayres, D.C.; Loike J.D. Lignons. Chemical, Bological and Clinical properties, Cambridge University Press: Cambridge, U.K., 1990; Chp. 3 and 4.
2. a) Belani, C.P.; Doyle, L.A.; Aisner, J. Etoposide: Current Status and Future perspectives in the management of malignant neoplasms. Cancer Chemoter. Pharmacol. 1994, 34 Suppl. S118-126.
3. b) Muggia, F.M. Cancer Chemoter. Pharmacol. 1994, 34 Suppl. S127-133.
4. a) Ward, R.S. Nat. Prod. Rep. 1995, 183-205.
5. b) San Feliciano, A.; Miguel del Corral, J.M.; Gordaliza, M.; Castro, M.A., Magn. Reson. Chem. 1993, 31, 868-880.
6. c) Whiting, D.A. Nat. Prod. Rep. 1990, 349-364.
7. Loike, J.D.; Brewer, C.F.; Sternlicht, H.; Gensler, W.J.; Horwitz, S.B. Cancer Res. 1978, 38, 2688-2693.
8. Loike, J.D.; Horwitz, S.B. Biochemistry 1976, 15, 5435-5443.
9. a) Long, B.H.; Musial, S.T.; Brattain, M.B.Biochemistry 1984, 23, 1183-1188.
10. b) Ross, R.; Rowe, T.; Glisson, B.; Yalowich, J.; Liu, F.Cancer Res. 1984, 44, 2857-2860.
11. Liu, S.Y.; Hwang, B.D.; Haruna, M.; Imakura, Y.; Lee, K.H.; Cheng, Y.C. Mol. Pharmacol. 1989, 36, 78-82.
12. Cho, S.J.; Tropsha, A.; Suffness, M.; Cheng, Y.C.; Lee, K.H. J. Med. Chem. 1996, 39, 1383-1395.
13. Cho, S.J.; Kashiwada, Y.; Bastow, K.F.; Cheng, Y.C.; Lee, K.H. J. Med. Chem. 1996, 39, 1396-1402.
14. a) Yang, C.M.; Deng, J.F.; Chen, C.F.; Chang, L.W.Biomed. Environ. Sci. 1994, 7, 259-265.
15. b) Souza, P.; Friedlander, M.; Wilde, C.; Kirsten, F.; Ryan, M. Am. J. Clin. Oncol. 1994, 17, 387-389.
16. c) Kobayashi, K.; Rotain, M.J. Cancer Chemoter. Pharmacol. 1994, 34 Suppl. S64-68.
17. a) Brewer, C.F.; Loike, J.D.; Horwitz, S.B.; Sternlicht, H.; Gensler, W.J. J. Med. Chem. 1979, 22, 215-221.
18. b) Jardine, I.; Strife, R.J.; Kozlowski, J. J. Med. Chem. 1982, 25, 1077-1081.
19. c) Zhou, X.M.; Lee, K.J.H.; Cheng, J.; Wu, S.S.; Chen, H.X.; Guo, X.; Cheng, Y.C.; Lee, K.H. J. Med. Chem. 1994, 37, 287-292.
20. Beard, A.R.; Drew, M.G.B.; Hilgard, P.; Hudson, B.D.; Mann, J.; Neidle, S.; Wong, L.F.T. Anti-Cancer Drug Design, 1987, 2, 247-252.
21. Biogenetic numbering according to Moss G.P. (1987, Paper to the Biochemistry Commitee of the International Union of Pure & Applied Chemistry) is used in this paper.
22. McCombie, S.N.; Tagat, J.R.; Metz, W.A.; Nazareno, D.; Puar, M.S.Tetrahedron 1993, 49, 8073-8086.
23. Tomioka, K.; Kubota, Y.; Koga, K. Tetrahedron 1993, 49, 1891-1900.
24. a) San Feliciano, A.; Gordaliza, M.; Miguel del Corral, J.M.; Castro, M.A.; García-Grávalos, M.D.; Ruiz-Lázaro, P. Planta Med. 1993, 59, 246-249.
25. b) Gordaliza, M.; Castro, M.A.; García-Grávalos, M.D.; Ruiz-Lázaro, P.; Miguel del Corral, J.M.; San Feliciano, A. Arch. Pharm. (Weinheim). 1994, 327, 175-179.
26. Gordaliza, M.; Miguel del Corral, J.M.; Castro, M.A.; López-Vázquez, M.L.; García, P.A.; San Feliciano, A.; García-Grávalos, M.D. Bioorg. Med. Chem. Lett. 1995, 5, 2465-2468.
27. Gordaliza, M.; Miguel del Corral, J.M.; Castro, M.A.; López-Vázquez, M.L.; San Feliciano, A.; García-Grávalos, M.D.; Carpy, A. Bioorg. Med. Chem. 1995, 3, 1203-1210.
28. Miguel del Corral, J.M.; Gordaliza, M.; Castro, M.A.; Morales, L.J.; López, J.L.; San Feliciano, A. J. Nat. Prod. 1995, 58, 870-877.
29. Ayres, D.C.; Harris, J.A.; Jenkins, P.N.; Phillips, L. J. Chem. Soc. Perkin I 1972, 1343-1355.
30. Freeman, F. Oxidation by Oxochromium (VI) Compounds. In Organic Syntheses by Oxidation with Metal Compounds, Mijs, W.J., De Jonge, C.R.H.I., Eds.; Plenum Press: New York, 1986; pp 41-108.
31. Mancuso, A.J.; Swern, D. Synthesis 1981, 165-198.
32. a) Miguel del Corral, J.M.; Gordaliza, M.; López, J.L.; Del Olmo, E.; Castro, M.A.; López, M.L. Helv. Chim. Acta 1995, 78, 1793-1796.
33. b) Beers, S.A.; Imakura, Y.; Dai, H.J.; Li, D.H.; Cheng, Y.C.; Lee, K.H. J. Nat. Prod. 1988, 57, 901-905.
34. Kocienski, P.J. Protecting groups, Thieme Foundations of Organic Chemistry Series. Georg Thieme Verlag: Stuttgart, 1994; pp 155-184.
35. Vedejs, E; Fuchs, P.L. J. Org. Chem. 1971, 36, 366-367.
36. San Feliciano, A.; Miguel del Corral, J.M.; Gordaliza, M.; Castro, M.A. Phytochemistry 1990, 29, 1335-1338.
37. National Cancer Institute, Bethesda, Maryland. Personal communication.
38. Haar, E. ter; Rosenkranz, H.S.; Hamel, E.; Day, B.W. Bioorg. Med. Chem. 1996, 4, 1659-1671.
39. Smissman, E.E.; Murray, R.J.; McChesney, J.D.J. Med. Chem. 1976, 19, 148-153.
40. Bergeron, R.J.; Cavanaugh, Jr P.F.; Kline, S.J.; Hughes, R.G.; Elliot, G.T.; Porter, C.W. Biochem. Biophys. Res. Commun. 1984, 121, 848-854.