triterpenoid pyrazines and benzopyrazines with cytotoxic activity

Journal of Natural Products

Volumn 70, Issue 4, 2007, Pages 526-532

  Urban, Milan ^a,b   Sarek, Jan ^a   Kvasnica, Miroslav ^a,b   Tislerova, Iva ^a   Hajduch, Marian ^c  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^c PALACKÝ UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ALLOBETULIN; ALLOBETULON; BENZOPYRAZINE DERIVATIVE; BETULIC ACID; BETULIN; BETULONIC ACID; CARBOXYL GROUP; DIHYDROBETULINIC ACID; DIHYDROBETULONIC ACID; DIKETONE; KETONE DERIVATIVE; METHYLBETULONATE; METHYLDIHYDROBETULONATE; PYRAZINE DERIVATIVE; TRITERPENOID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL LINE; COMPARATIVE STUDY; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG SCREENING; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; LYMPHATIC LEUKEMIA; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; LEUKEMIA, T-CELL; MOLECULAR STRUCTURE; PYRAZINES; STRUCTURE-ACTIVITY RELATIONSHIP; TRITERPENES; TUMOR CELLS, CULTURED;

EID: 34249307501     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np060436d     Document Type: Article

References (33)

1. Dzubak, P.; Hajduch, M.; Vydra, D.; Hustova, A.; Kvasnica, M.; Biedermann, D.; Markova, L.; Urban, M.; Sarek, J. Nat. Prod. Rep. 2006, 23, 394-411.
2. Pettit, G. R.; Inoue, M.; Ramano, Y.; Herald, D. L.; Arm, C.; Dufresne, C.; Christie, N. D.; Schmidt, J. M.; Doubek, D. L.; Krupa, T. S. J. Am. Chem. Soc. 1988, 110, 2006-2007.
3. Heathcock, C. H.; Smith, S. C. J. Org. Chem. 1994, 59, 6828-6839.
4. Kramer, A.; Ulimann, U.; Winterfeldt, E. J. Chem. Soc., Perkin Trans. 1 1993, 2865-2867.
5. Morzycki, J. W.; Gryszkiewicz, A.; Lotowski, Z.; Szczepek, W. J. Collect. Czech. Chem. Commun. 1998, 63, 1589-1596.
6. Fujioka, T.; Kashiwada, Y.; Kilkuskie, R. E.; Cosentino, L. M.; Ballas, L. M.; Jiang, J. B.; Janzen, W. P.; Chen, I. S.; Lee, K. H. J. Nat. Prod. 1994, 57, 243-247.
7. Evers, M.; Poujade, C.; Soler, F.; Ribeill, Y.; James, C.; Lelicevre, Y.; Gueguen, J. C.; Reisdorf, D.; Morize, I.; Pauwels, R.; De Clercq, E.; Henin, Y.; Bousseau, A.; Mayaux, J. F.; Le Pecq, J. B.; Dereu, N. J. Med. Chem. 1996, 39, 1056-1068.
8. Setzer, W. N.; Setzer, M. G.; Bates, R. B.; Jackes, B. R. Planta Med. 2000, 66, 176-177.
9. Costantini, P.; Jacotot, E.; Decaudin, D.; Kroemer, G. J. Natl. Cancer Inst. 2000, 92, 1042-1053.
10. 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.; Gupta, T. K. D.; Pezzuto, J. M. Nat. Med. 1995, 1, 1046-1051.
11. Jeong, H. J.; Chai, H. B.; Park, S. Y.; Kim, D. S. H. L. Bioorg. Med. Chem. Lett. 1999, 9, 1201-1204.
12. Fulda, S.; Jeremias, I.; Ketsch, T.; Debatin, K. M. Int. J. Cancer 1999, 82, 435-441.
13. Kim, Y. K.; Yoon, S. K.; Ryu, S. Y. Planta Med. 2000, 66, 485-486.
14. Schmidt, M. L.; Kuzmanoff, K. L.; Ling-Indeck, L.; Pezzuto, J. M. Eur. J. Cancer 1997, 33, 2007-2010.
15. Fulda, S.; Jeremias, I.; Pietsch, T.; Debatin, K. M. Klin. Pediatr. 1999, 211, 319-322.
16. Ryu, S. Y.; Choi, S. U.; Lee, S. H.; Lee, Ch. O.; No, Z.; Ahn, J. W. Arch. Pharm. Res. 1994, 17, 375-377.
17. Hajduch, M.; Sarek, J. PCT Intl. Patent Appl. Publ. WO 01/90046, CAN 136:6179, 2001.
18. Sarek, J.; Klinot, J.; Brazinova, S.; Dzubak, P.; Klinotova, E.; Noskova, V.; Krecek, V.; Korinkova, J.; Thomson, J. O.; Janostakova, J.; Wang, S.; Parsons, S.; Fischer, P. M.; Zhelev, N. Z.; Hajduch, M. J. Med. Chem. 2003, 46, 5402-5415.
19. You, Y.-J.; Kim, Y; Nam, N.-H.; Ahn, B.-Z. Bioorg. Med. Chem. Lett. 2003, 13, 3137-3140.
20. Reddy, R. P.; Ravindranath, A.; Sudhakar, B.; Ramaiah, T. S.; Rao, M. V. J. Ind. Chem. Soc. 1988, 65, 688-690.
21. Huneck, S. Chem. Ber. 1965, 98, 1837-1857.
22. Noskova, V.; Dzubak, P.; Kuzmina, G.; Ludkova, A.; Stehlik, D.; Trojanec, R.; Janostakova, A.; Korinkova, G.; Mihal, V.; Hajduch, M. Neoplasma 2002, 49, 418-425.
23. Sejbal, J.; Klinot, J.; Prouva, J.; Vystrcil, A. Collect. Czech. Chem. Commun. 1986, 51, 118-127.
24. Pradhan, B. P.; Ghosh, P. Ind. J. Chem., Sect. B 1993, 32, 1068-1069.
25. Urban, M.; Sarek, J.; Klinot, J.; Korinkova, G.; Hajduch, M. J. Nat. Prod. 2004, 67, 1100-1105.
26. Kvasnica, M.; Tislerova, I.; Sarek, J.; Sejbal, J.; Cisarova, I. Collect. Czech. Chem. Commun. 2005, 70, 1447-1464.
27. Urban, M.; Sarek, J; Tislerova, I; Dzubak, P.; Hajduch, M. Bioorg. Med. Chem. 2005, 13, 5527-5535.
28. Hui, W.-H.; Li, M.-M. J. Chem. Soc., Perkin Trans. 1 1977, 8, 897-904.
29. Otsuka, H.; Fujioka, S.; Komiya, T.; Goto, M.; Hirmatsu, Y.; Fujimora, H. Chem. Pharm. Bull. 1981, 29, 3099-3104.
30. Hashimoto, F.; Kashiwada, Y.; Cosentino, L. M.; Chen, C. H.; Garrett, P. E.; Lee, K. H. Bioorg. Med. Chem. 1997, 5, 2133-2143.
31. Li, T. S.; Wang, J. X.; Zheng, X. J. Chem. Soc., Perkin Trans. 1 1998, 3957-3965.
32. Biedermann, D.; Sarek, J.; Klinot, J.; Hajduch, M.; Dzubak, P. Synthesis 2005, 7, 1157-1163.
33. Huneck, S. Tetrahedron Lett. 1963, 4, 1977-1980.