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Acylfulvenes, a new class of potent antitumor agents

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Abstract

Acylfulvene, derived from the sesquiterpene illudin S by treatment with acid (reverse Prins reaction), is far less reactive to thiols than illudin S. However, it is reduced readily to an aromatic product, in the same way as illudin S. This may explain its greatly improved therapeutic index compared to that of the parent compound.

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Literatur

  1. McMorris, T. C., and Anchel, M., J. Am. chem. Soc.85 (1963) 831.

    Article  CAS  Google Scholar 

  2. McMorris, T. C., and Anchel, M., J. Am. chem. Soc.87 (1965) 1594.

    Article  CAS  PubMed  Google Scholar 

  3. McMorris, T. C., Moon, S., and Ungab, G. J. nat. Products52 (1989) 380.

    Article  CAS  Google Scholar 

  4. Nakanishi, K., Ohashi, M., Tada, M., and Yamada, Y., Tetrahedron21 (1965) 1231.

    Article  CAS  PubMed  Google Scholar 

  5. Matsumoto, T., Shirahama, H., Ichihara, A., Fukuoka, Y., Takahashi, Y., Mori, Y., and Watanabe, M., Tetrahedron21 (1965) 2671.

    Article  CAS  PubMed  Google Scholar 

  6. Maretíc, Z., Russell, F., and Golobic, V., Toxicon13 (1975) 379.

    Article  PubMed  Google Scholar 

  7. French, A. L., and Garrettson, L. K., Clin. Toxic.26 (1988) 81.

    CAS  Google Scholar 

  8. Kelner, M. J., McMorris, T. C., Beck, W. T., Zamora, J. M., and Taetle, R., Cancer Res.47 (1987) 3186.

    CAS  PubMed  Google Scholar 

  9. McMorris, T. C., Kelner, M. J., Chadha, R. K., Siegel, J. S., Moon, S., and Moya, M., Tetrahedron45 (1989) 5433.

    Article  CAS  Google Scholar 

  10. Kelner, M. J., McMorris, T. C., and Taetle, R., J. natl Cancer Inst.82 (1990) 1562.

    Article  CAS  PubMed  Google Scholar 

  11. McMorris, T. C., Kelner, M. J., Wang, W., Moon, S., and Taetle, R., Chem. Res. Toxic.3 (1990) 574.

    Article  CAS  Google Scholar 

  12. McMorris, T. C., Kelner, M. J., Wang, W., Estes, L. A., Montoya, M. A., and Taetle, R., J. Org. Chem.57 (1992) 6876.

    Article  CAS  Google Scholar 

  13. Fahey, R. C., Myers, P. A., and DiStefano, D. L., Bioorganic Chem.9 (1980) 293.

    Article  CAS  Google Scholar 

  14. Varki, N. M., Tseng, A., Vu, T. P., and Estes, L. A., Anticancer Res.10 (1990) 637.

    CAS  PubMed  Google Scholar 

  15. Kelner, M. J., McMorris, T. C. Estes, L. A., Montoya, M. A., Starr, R., Samson, K., and Taetle, R., Cancer Res. (1995) in press.

  16. Tanaka, K., Inoue, T., Kadota, S., and Kikuchi, T., Xenobiotica22 (1992) 33.

    Article  CAS  PubMed  Google Scholar 

  17. Fisher, J. F., and Aristoff, P. A., Prog. Drug Res.32 (1988) 441.

    Google Scholar 

  18. Harttig, U., Anke, T., Scherer, A., and Steglich, W., Phytochemistry29 (1990) 3942.

    Article  CAS  Google Scholar 

  19. Weinreb, S. M., McMorris, T. C., and Anchel, M., Tetrahedron Lett.38 (1971) 3489.

    Article  Google Scholar 

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McMorris, T.C., Kelner, M.J., Wang, W. et al. Acylfulvenes, a new class of potent antitumor agents. Experientia 52, 75–80 (1996). https://doi.org/10.1007/BF01922420

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  • DOI: https://doi.org/10.1007/BF01922420

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