Syntheses and cytotoxicity evaluation of bis(indolyl)thiazole, bis(indolyl)pyrazinone and bis(indolyl)pyrazine: Analogues of cytotoxic marine bis(indole) alkaloid

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 2, 2000, Pages 363-371

  Jiang, Biao ^a   Gu, Xiao Hui ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Alkaloiods; Antitumor compounds; Cytotoxins; Substituent effects

Indexed keywords

2,4 BIS(3' INDOLYL)THIAZOLE; ALKALOID DERIVATIVE; ANTINEOPLASTIC AGENT; PYRAZINE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; DRUG CYTOTOXICITY; DRUG SYNTHESIS; LEUKEMIA CELL LINE;

ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDOLES; MOLECULAR STRUCTURE; SPECTRUM ANALYSIS; TUMOR CELLS, CULTURED;

EID: 0034000795     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00290-4     Document Type: Article

References (28)

1. Alvarez M., Salas M. Heterocycles. 32:1991;1391.
2. Faulkner D.J. Nat. Prod. Rep. 15:1998;113.
3. Sakemi S., Sun H.H. J. Org. Chem. 56:1991;4304.
4. Sun, H. H.; Sakemi, S.; Gunasekera, S.; Kashman, Y.; Lui, M.; Burres, N.; McCarthy, P. U.S. Patent 4970226 [Chem. Abstr. 1991, 115, 35701z].
5. Kawasaki I., Yamashita M., Ohta S. Chem. Pharm. Bull. 44:1996;1831.
6. Mancini I., Guella G., Debitus C., Waikedre J., Pietra F. Helv. Chim. Acta. 79:1996;2075.
7. Blatter H.M., Lukaszewski H., De Stevens G. J. Am. Chem. Soc. 83:1961;303.
8. Taylor E.C., Zoltewicz J.A. J. Am. Chem. Soc. 82:1960;2656.
9. Chihiro M., Nagamoto H., Takemura I., Kitano K., Komatsu H., Sekiguchi K., Tabusa F., Mori T., Tominaga M., Yabuuchi Y. J. Med. Chem. 38:1995;353.
10. Hodson H.F., Madge D.J., Slawin A.N.Z., Widdowson D.A., Williams D.J. Tetrahedron. 50:1994;1899.
11. Ketcha D.M., Gribble G.W. J. Org. Chem. 50:1985;5451.
12. King L.C., Ostrum G.K. J. Org. Chem. 29:1964;3459.
13. Braekman J.C., Daloze D., Stoller C. Bull. Soc. Chim. Belg. 96:1987;809.
14. Grever M.R., Schepartz S.A., Chabner B.A. Seminars in Oncology. 19:1992;622.
15. Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., Hose C., Langley J., Cronise P., Vaigro-Woiff A., Gray-Goodrich M., Campbell H., Mayo J., Boyd M.R. J. Natl. Cancer Inst. 83:1991;757.
16. Boyd, M. R.; Paull, K. D.; Rubinstein, L. R. In Cytotoxic Anticancer Drugs: Models and Concepts for Drug Discovery, Valeriote, F. A.; Corbett, T.; Baker, L., Eds., Kluwer Academic Publishers: Amsterdam, 1992, pp 11.
17. Hollingshead M.G., Alley M.C., Camalier R.F., Abbott B.J., Mayo J.G., Malspeis L., Grever M.R. Life Sci. 57:1995;131.
18. Nakaike S., Yamagishi T., Samata K., Nishida K., Inazuki K., Ichihara T., Migita Y., Otomo S., Aihara H., Tsukagoshi S. Cancer Chemother. Pharmacol. 253:1989;135.
19. Ishida T., Mihara Y., Hama Y., Hanatani A., Tarui M., Doi M., Nakaike S., Kitamura K. Chem. Pharm. Bull. 46:1998;739.
20. Gunasekera S.P., McCarthy P.J., Kelly-Borges M. J. Nat. Prod. 57:1994;1437.
21. Wright A.E., Pomponi S.A., Cross S.S., MaCarthy P. J. Org. Chem. 57:1992;4772.
22. Bergman J., Backvall J.E., Lindstrom J.O. Tetrahedron. 29:1973;971.
23. Moody, C. J.; Ward, J. G. J. Chem. Soc. Perkin Trans 1 1984, 2903.
24. Nakajima M., Loeschorn C.A., Cimbrelo W.E., Anselme J.P. Org. Pre. Proc. Int. 12:1980;265.
25. Zbiral von E., Stroh J. Liebigs Ann. Chem. 727:1969;231.
26. Speeter M.E., Anthony W.C. J. Am. Chem. Soc. 76:1954;6208.
27. Bradbury R.H., Griffiths D., Rivert J.E. Heterocycles. 31:1990;1647.
28. Paull K.D., Shoemaker R.H., Hodes L., Monks A., Scudiero D.A., Rubinstein L., Plowman J., Boyd M.R. J. Natl. Cancer Inst. 81:1989;1088.