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Cephalosporins containing carbonate functions at positions 3 and 7

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Sulfones of 7β-alkoxycarbonyloxy-substituted cephalosporanic acid tert-butyl esters were synthesized by reduction of 7-oxocephalosporanic acid tert-butyl ester, acylation of the intermediate 7β-hydroxycephalosporanate with 2,2,2-trichloroethyl chloroformate or di-tert-butyl pyrocarbonate, and oxidation of the sulfur atom. Sulfones of 7α-chloro- and 7-alkylidene-substituted 3-alkoxycarbonyloxymethylcephalosporanic acid tert-butyl esters were obtained by replacement of the bromine atom in tert-butyl 3-bromomethylcephalosporanates with hydroxy group and acylation of the latter with chlorocarbonic esters. The cytotoxic activity of the synthesized substances was studied in vitro and also their ability to inhibit elastase.

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References

  1. J. C. Sheehan, Y. S. Lo, and D. R. Ponzi,J. Org. Chem.,42, 1012 (1977).

    CAS  Google Scholar 

  2. 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, 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  CAS  Google Scholar 

  3. S. K. Shah, K. A. Brause, G. O. Chandler, P. E. Finke, B. M. Ashe, H. Weston, W. B. Knight, A. L. Maycock, and J. B. Doherty,J. Med. Chem.,33, 2529 (1990).

    Article  CAS  Google Scholar 

  4. G. A. Veinberg, L. N. Petrulyanis, N. Grigan, I. V. Turovskii, D. I. Musel', and E. Lukevics,Khim. Geterotsikl. Soedin., No. 1, 110 (1996).

    Google Scholar 

  5. R. P. Alexander, N. R. A. Beeley, M. O'Driscoll, F. P. O'Neill, T. A. Millican, A. J. Pratt, and F. W. Willenbrock,Tetrah. Lett.,32, 3269 (1991).

    CAS  Google Scholar 

  6. L. N. Jungheim, T. A. Shepherd, and J. K. Kling,Heterocycles,35, 339 (1993).

    CAS  Google Scholar 

  7. S. Mobashery and M. Johnston,Tetrah. Lett.,27, 3333 (1986).

    Article  CAS  Google Scholar 

  8. G. A. Veinberg, I. Shestakova, N. Grigan, D. Musel, I. Kanepe, I. Domrachova, V. Grigoryeva, O. Zharkova, I. Turovskis, I. Kalvinsh, A. Strakovs, and E. Lukevics,Eur. J. Med. Chem.,3, 755 (1998).

    Google Scholar 

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Authors
  1. G. Veinberg
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  2. M. Vorona
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  3. N. Grigan
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  4. I. Kanepe
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  5. I. Shestakova
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  6. A. Strakov
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  7. E. Lukevics
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Additional information

Latvian Institute of Organic Synthesis, Riga LV-1006

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 847–853, June, 2000.

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Veinberg, G., Vorona, M., Grigan, N. et al. Cephalosporins containing carbonate functions at positions 3 and 7. Chem Heterocycl Compd 36, 744–750 (2000). https://doi.org/10.1007/BF02297686

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  • DOI: https://doi.org/10.1007/BF02297686

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