Synthesis of betulinic acid derivatives with activity against human melanoma

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 13, 1998, Pages 1707-1712

  Kim, Darrick S H L ^a   Pezzuto, John M ^a   Pisha, Emily ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BETULIC ACID;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CHEMICAL MODIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MELANOMA; STRUCTURE ACTIVITY RELATION;

EID: 0032493481     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00295-9     Document Type: Article

References (23)

1. 1. Pisha, E.; Chai, H.; Lee, I.-S.; Chagwedera, T. E.; Farnsworth, N. R.; Cordell, G. A.; Beecher, C. W. W.; Fong, H. H. S.; Kinghorn, A. D.; Brown, D. M.; Wani, M. C.; Wall, M. E.; Hieken, T. J.; Das Gupta, T. K.; Pezzuto, J. M. Nature Medicine 199S, 1, 1046.
2. 2. Fulda, S.; Friesen, C; Los, M.; Scaffidi, G.; Mier, W.; Benedict, M.; Nunez, M.; Krammer, P. H.; Peter, M. E.; Debatin, K. M. Cancer Res. 1997, 57, 4956.
3. 3. Lin, Z., Raman, A.; Km, D. S. H. L. J. Pharm. Pharmacol. 1997, 49, 35.
4. 4. Recio, M. C.; Giner, R. M.; Manz, S.; Gueho, J.; Julien, H. R.; Hostettmann, K.; Rios, J. L. Planta Med. 1995, 61, 9.
5. 5. Yasukawa, K.; Takido, M.; Matsumoto, T.; Takeuchi, M.; Nakagawa, S. Oncology 1991, 48, 72.
6. 6. O'Connell, M. M.; Bentley, M. D.; Campbell, C. S.; Cole, B. J. W. Phytochemistry 1988, 27, 2175.
7. 7. Kim, D. S. H. L.; Chen, Z.; Nguyen, v. T.; Pezzuto, J. M.; Qiu, S.; Lu, Z.-Z. Synth. Commun. 1997, 27, 1607.
8. 8. Likhitwitayawuid, K.; Angerhofer, C. K.; Cordell, G. A.; Pezzuto, J. M. J. Nat. Prod. 1993, 58, 1468.
9. 9. Pakrashi, S. C.; Bhattacharyya, J.; Mookerjee, S.; Samanta, T. B. Phytochemistry 1968, 7, 461.
10. 10. Karabatsos, G. J.; Hsi, N. Tetrahedron 1967, 23, 1079.
11. 11. Karabatsos, G. J.; Taller, R. A. Tetrahedron 1968, 24, 3347.
12. 12. Lane, C. F. Synthesis, 1975, 135.
13. 13. Borch, R. F.; Berstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897.
14. 14. Hutchins, R.; Nicholas, R. N. Org. Prep. Proc. Int. 1979, 11, 201.
15. 15. Tomioka, H.; Takai, K; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605.
16. 16. Kanemoto, S.; Oshima, K.; Matsubara, S.; Kazuhiko, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 2185.
17. 17. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 20, 399.
18. 18. Lindlar, H.; Dubuis, R. Org. Synth. Coll. Vol. V, 880.
19. 19. McEwen, A. B.; Guttier, M. J.; Maier, W. F.; Laine, R. M.; Shvo, Y. J. Org. Chem. 1983, 48, 4436.
20. 20. Harmon, R. E.; Parsons, J. L.; Cooke, D. W.; Gupta, S. K.; Schoolenberg, J. J. Org. Chem. 1969, 34, 3684.
21. 21. Nicholas, K. M. J. Am. Chem. Soc. 1975, 97, 3254.
22. 22. Compound 16 was prepared from betulinic acid by treating with azomethine in diethyl ether at rt.
23. 23. Compound 18 was prepared from lupeol by refluxing with benzoyl chloride in pyridine over night.