Facile and improved synthesis of 4β-aminopodophyllotoxin congeners

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 21, 1998, Pages 3097-3100

  Kamal, Ahmed ^a   Gayatri, N Lakshmi ^a   Rao, N Venugopal ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

4BETA AMINO 4' O DEMETHYLPODOPHYLLOTOXIN; 4BETA AMINOPODOPHYLLOTOXIN; GYRASE INHIBITOR; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONFORMATIONAL TRANSITION; DNA STRAND BREAKAGE; DRUG CONFORMATION; DRUG SYNTHESIS; ENZYME INHIBITION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0032213479     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00570-8     Document Type: Article

References (34)

1. 1. Lee, K. H. In Human Medicinal Agents from Plants ; American Chemical Society, Symposium Series; Kinghorn, A. D.; Balandrin, M., Eds.; American Chemical Society: Washington, DC, 1993; pp 170-190.
2. 2. MacRae, W. D.; Hudson, J. B.; Towers, B. H. N. Planta Medica 1993, 55, 531.
3. 3. Jardine, I. In Anticancer Agents based on Natural Product Models; Cassady, J. M.; Douros, J. Eds.; Academic: New York, 1980; pp 319-35, and references cited therein.
4. 4. (a) Lee, K.; Beers, S. A.; Mori, M.; Wang, Z.; Kuo, Y.; Li, L.; Liu, S.; Chang, Y.; Han, F.; Cheng, Y. J. Med. Chem. 1990, 33, 1364;
5. (b) Wang, Z.; Kuo, Y.; Schnur, D.; Bowen, J. P.; Liu, S.; Han, F.; Chang, J.; Cheng, Y.; Lee, K. J. Med. Chem. 1990, 33, 2660;
6. (c) Stahelin, H.; Von Wartburg, A. Prog. Drug. Res. 1989, 33, 169;
7. (d) Doyle, T. W. Etoposide (VP-16) Current Status and New Developments : Academic: New York, 1984.
8. 5. Macdonald, T. L.; Lehnert, E. K.; Loper, J. T.; Chow, K. C.; Ross, W. E. In DNA Topoisomerases in Cancer; Potmesil, M.; Kohn K. W. Eds.; Oxford University: New York, 1991; pp 199-214 , and references therein.
9. 6. (a) Ward, R. S. Synthesis 1992, 719, and references therein;
10. (b) Sauliner, M. G.; LeBoulluec, K. L.; McGee, D. P. C.; Long, B. H.; Crosswell., A. R.; Vyas, D. M. Bioorg. Med. Chem. Lett. 1993, 3, 1619;
11. (c) Terrada, T.; Fujimoto, K.; Nomura, M.; Yamazaki, R.; Shibata, J.; Sugimoto, Y.; Yamada, Y. J. Med Chem. 1993, 36, 1689;
12. (d) Bush, J. E.; Jones, D. W. J. Chem. Soc., Chem. Commun. 1993, 1200;
13. (e) Tomioka, K.; Kubota, Y.; Kogo, K. Tetrahedron Lett. 1993, 49, 1891;
14. (f) Watt, P. M.; Hickson, I. D. Biochem. J. 1994, 303, 681, and references therein;
15. (g) Hitosuyangi, Y.; Kobayashi, M.; Takeya, K.; Itokawa, H. J. Chem. Soc., Perkin Trans. 1 1995, 1387;
16. (h) Hadimani, S. B.; Tanpure, R. P.; Bhaat, S. V. Tetrahedron Lett. 1996, 37, 4791;
17. (i) Tawa, R.; Takami, M.; Imakura, Y.; Lee, K. H.; Sakuri, H. Bioorg. Med. Chem. Lett. 1997, 7, 489.
18. 7. (a) Lee, K. H.; Imakura, Y.; Haruna, M.; Beers, S. A.; Thurston, L. S.; Dai, H. J.; Chen, C.-H. J. Nat. Prod. 1989, 52, 606;
19. (b) Zhang, Y. L.; Shen, Y-C.; Wang, Z.-Q; Chen, H.-X; Guo, X.; Cheng, Y.-C.; Lee, K.-H. J. Nat. Prod. 1992, 55, 1100;
20. (c) Zhang, Y. L.; Guo, Z.; Cheng, Y. C.; Lee, K. H. J. Med. Chem. 1994, 37, 446.
21. 8. Ji, Z.; Wang, H. -K.; Bastow, K. F.; Zhu, S. J.; Cheng, Y. -C.; Lee, K.-H. Bioorg. Med. Chem. Lett. 1997, 7, 607.
22. 9. (a) Kamal, A.; Atchison, K.; Daneshtalab, M.; Micetich, R. G. Anti-cancer Drug Design 1995, 10, 545.
23. 10. Kamal, A.; Gayatri, N. L. Tetrahedron Lett. 1996, 37, 3359;
24. (b) Kamal, A.; Damayanthi, Y. Bioorg. Med. Chem. Lett. 1997, 7, 657;
25. (c) Kamal, A.; Laxminarayana, B.; Lakshmi Gayatri, N. Tetrahedron Lett. 1997, 38, 6871.
26. 11. (a) Indian Patent Application No. 1712/DEL/97 June 24, 1997;
27. (b) Kamal, A.; Rao, M. V.; Arifuddin, M.; Gayatri, N. L., part of the work presented in the Chira-Tech 1997 Conference, Philadelphia, USA;
28. (c) Kamal, A.; Gayatri, N. L.; Laxman, E.; Arifuddin, M.; Laxman, N., unpublished results.
29. 12. Kuhn, M.; Keller-Juslen, C; von Wartburg, A. Helv. Chem. Acta. 1959, 52, 948.
30. 13. Kamal, A.; Rao, N. V.; Laxman, E. Tetrahedron Lett. 1997, 38, 6945.
31. 14. Vickery, E. H.; Pahler, L. F.; Eisenbraun, E. J. J. Org. Chem. 1979, 44, 4444.
32. 15. Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. J. Org. Chem. 1979, 44, 1247.
33. 16. Deley, L.; Meresse, P.; Bertounesque, E; Monnere, C. Tetrahedron Lett. 1997, 38, 2673.
34. + ]