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Synthesis and anticancer properties of 7α-chloro-3-methyl-1,1-dioxoceph-3-em-4-carboxylic acid esters

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The tert-butyl esters of 3-azidomethyl-, 3-isocyanatomethyl-, 3-chloromethyl-, and 3-p-nitrophenylvinyl-7α-chloro-1,1-dioxoceph-3-em-4-carboxylic acid, and also esters of 7α-chloro-3-methyl-1,1-dioxoceph-3-em-4-carboxylic acid, and of 7α-chloro-3-methyl-2-dimethylaminomethylene-1,1-dioxoceph-3-em-4-carboxylic acid have been synthesized. Results of cytotoxic screening of these compounds in relation to cancer and normal cells in vitro are correlated and analyzed.

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References

  1. G. Veinberg, M. Vorona, I. Shestakova, I. Kanepe, and E. Lukevics, Curr. Med. Chem., 10, 1741 (2003).

    Article  PubMed  CAS  Google Scholar 

  2. J. B. Doherty, B. M. Ashe, L. W. Argenbright, P. L. Barker, R. J. Bonney, G. O. Chandler, M. E. Dahlgren, C. P. Dorn, Jr., P. E. Finke, R. A. Firestone, D. Fletcher, W. K. Hagmann, R. Mumford, L. O’Grady, A. L. Maycock, J. M. Pisano, S. K. Shah, K. R. Thompson, and M. Zimmerman, Nature, 322, 192 (1986).

    Article  PubMed  ADS  CAS  Google Scholar 

  3. W. T. Han, A. K. Trehan, J. J. K. Wright, M. E. Federici, S. M. Seller, and N. A. Meanwell, Bioorg, Med. Chem., 3, 1123 (1995).

    Article  CAS  Google Scholar 

  4. A. D. Borthwick, G. Weingarten, T. M. Haley, M. Tomaszewski, W. Wang, Z. Hu, J. Bedard, H. Jin, L. Yuen, and T. S. Mansour, Bioorg. Med. Chem. Lett., 8, 365 (1998).

    Article  PubMed  CAS  Google Scholar 

  5. N. E. Zhou, D. Guo, G. Thomas, A. V. N. Reddy, J. Kaleta, E. Prisima, R. Menard, R. G. Micetich, and R. Singh, Bioorg. Med. Chem. Lett., 13, 139 (2003).

    Article  PubMed  CAS  Google Scholar 

  6. J. B. Doherty, B. M. Ashe, P. L. Barker, T. J. Blacklock, J. W. Butcher, G. O. Chandler, M. E. Dahlgren, P. Davies, C. P. Dorn, Jr., P. E. Finke, R. A. Firestone, W. K. Hagmann, T. Halgren, W. B. Knight, A. L. Maycock, M. A. Navia, L. O’Grady, J. M. Pisano, S. K. Shah, K. R. Thompson, H. Weston, and M. Zimmerman, J. Med. Chem., 33, 2513 (1990).

    Article  PubMed  CAS  Google Scholar 

  7. G. A. Veinberg, I. Shestakova, N. Grigan, D. Musel, I. Kanepe, I. Domrachova, V. Griroryeva, O. Zharkova, I. Turovskis, I. Kalvinsh, A. Strakovs, and E. Lukevics, Eur. J. Med. Chem., 33, 755 (1998).

    Article  CAS  Google Scholar 

  8. K. Taniguchi, P. Yang, J. Jett, E. Bass, R. Meyer, Y. Wang, C. Deschamps, and W. Liu, Clin. Cancer Res., 8, 1115 (2002).

    PubMed  CAS  Google Scholar 

  9. F. Nozawa, M. Hirota, A. Okabe, M. Shibata, T. Iwamura, Y. Haga, and M. Ogawa, J. Surg. Res., 94, 153 (2000).

    Article  PubMed  CAS  Google Scholar 

  10. K. Iwatsuki, E. Kumara, T. Yoshimine, H. Nakagawa, M. Sato, and T. Hayakawa, Neurol. Res., 22, 465 (2000).

    PubMed  CAS  Google Scholar 

  11. G. Veinberg, M. Vorona, D. Musel, H. Kazhoka, I. Shestakova, I. Kanepe, I. Domracheva, A. Strakovs, and E. Lukevits, Khim. Geterotsikl. Soedin., 1504, (1998). [Chem. Heterocycl. Comp., 34, 1276 (1998)].

    Google Scholar 

  12. G. Veinberg, R. Bokaldere, K. Dikovskaya, M. Vorona, D. Musel, H. Kazhoka, I. Turovskis, I. Shestakova, I. Kanepe, I. Domracheva, and E. Lukevics, Khim. Geterotsikl. Soedin., 1494 (1998). [Chem. Heterocycl. Comp., 34, 1266 (1998)].

    Google Scholar 

  13. N. Grigan, G. Veinberg, I. Shestakova, I. Kanepe, and E. Lukevics, Khim. Geterotsikl. Soedin., 1424 (2000). [Chem. Heterocycl. Comp., 36, 1232 (2000)].

    Google Scholar 

  14. G. Veinberg, M. Vorona, N. Grigan, I. Kanepe, I. Shestakova, A. Strakovs, and E. Lukevics, Khim. Geterotsikl. Soedin., 847 (2000). [Chem. Heterocycl. Comp., 36, 744 (2000)].

    Google Scholar 

  15. M. Alpegiani, A. Baici, P. Bissolino, P. Carminati, G. Cassinelli, S. Del Nero, G. Franceschi, P. Orezzi, E. Perrone, V. Rizzo, and N. Sacchi, Eur. J. Med. Chem., 27, 875 (1992).

    Article  CAS  Google Scholar 

  16. W. H. W. Lunn and P. A. Hipskind, Tetrahedron Lett., 33, 6291 (1992).

    Article  CAS  Google Scholar 

  17. US Department of Health and Human Services, Guidance Document on Using in vitro Data to Estimate in vivo Starting Doses for Acute Toxicity, National Institute of Health (2001).

  18. D. J. Fast, R. C. Lynch, and R. W. Leu, J. Leukocyt. Biol., 52, 255 (1992).

    CAS  Google Scholar 

  19. P. J. Freshney, in Culture of Animal Cells (A Manual of Basic Technique), Wiley-Liss, New York (1994). p. 296.

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 259–273, February, 2007.

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Vorona, M., Veinberg, G., Shestakova, I. et al. Synthesis and anticancer properties of 7α-chloro-3-methyl-1,1-dioxoceph-3-em-4-carboxylic acid esters. Chem Heterocycl Compd 43, 207–219 (2007). https://doi.org/10.1007/s10593-007-0033-x

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  • DOI: https://doi.org/10.1007/s10593-007-0033-x

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