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Synthesis of cephalosporins carrying isoxazolyl acetamido and related side chains

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Starting from 3,5-dimethylisoxazole the carboxylic acids I and V, the amino acids VIII (L-) and IX (D-), and the ureido acids X (L-) and XI (D-) were prepared, which were used for the synthesis of the new cephalosporins XVIIb, XXa-c (L-), and XXIb (D-). Thein vitro antibacterial activity of these semi-synthetic antibiotics was studied. The resorption of XVIIb was investigated in mice.

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References

  1. K. C. Kwan and J. D. Rogers, Antibiotics Containing Beta-Lactame Structure, II. Pharmacokinetics of β-Lactam Antibiotics, A. L. Demain and N. A. Solomon (eds), Berlin, Springer Verlag (1983), p. 278.

    Google Scholar 

  2. E. M. Gordon and R. B. Sykes, Chemistry and Biology of β-Lactam Antibiotics. Cephamycin Antibiotics, R. B. Morin and M. Gorman (eds.), Academic Press, New York (1982), p. 199.

    Google Scholar 

  3. Y. Nishitani, T. Aoki, T. Yoshida, and W. Nagata, J. Antibiot.,41, 316 (1988).

    Google Scholar 

  4. G. Nannini, E. Perrone, D. Severino, A. Bedeschi, G. Biasoli, G. Meinardi, and A. Bianchi, J. Antibiot.,34, 412 (1981).

    Google Scholar 

  5. P. Actor, J. Uri, J. R. Guarini, I. Zajac, L. Phillips, C. S. Sachs, R. M. DeMarinis, J. R. E. Hoover, and J. Weisbach, J. Antibiot.,28, 471 (1975).

    Google Scholar 

  6. I. Miskolczi, F. Sztaricskai, P. Herczegh, R. Bogncr, and I. Koczka, J. Antibiot.,38, 1273 (1985).

    Google Scholar 

  7. I. Miskolczi, F. Sztaricskai, and R. Bogncr, Org. Prep. Proc. Int.,14, 233 (1982).

    Google Scholar 

  8. W. J. Wheeler, D. R. Finley, R. J. Messenger, R. Koehler, and J. T. Ott, J. Antibiot.,39, 121 (1986).

    Google Scholar 

  9. E. Nakayama, K. Fujimoto, Sh. Muramatsu, and J. Ide, J. Antibiot.,45, 1193 (1992).

    Google Scholar 

  10. A. Sala, D. Chiarino, M. Napoletano, E. Albini, A. Carenzi, and D. B. Bella, J. Antibiot.,40, 1555 (1987).

    Google Scholar 

  11. F. Nakayama, K. Watanabe, M. Miyauchi, K. Fujimoto, and J. Ide, J. Antibiot.,43, 1123 (1990).

    Google Scholar 

  12. N. K. Kochetkov, E. D. Homutova, and M. V. Bazilevskij, Zh. Obshch. Khim.,38, 2736 (1958).

    Google Scholar 

  13. A. March, Compt. Rend.,132, 698 (1901).

    Google Scholar 

  14. S. D. Sokolov and N. K. Kochetkov, Zh. Obshch. Khim.,33, 1192 (1963).

    Google Scholar 

  15. V. F. Pozdnev, Khim. Prirodn. Soed., N6, 764 (1974).

    Google Scholar 

  16. R. M. DeMarinis, J. R. E. Hoover, G. L. Dunn, P. Actor, J. V. Uri, and J. A. Weisbach, J. Antibiot.,28, 412 (1075).

    Google Scholar 

  17. W. J. Gottstein, A. H. Eachus, P. F. Misco, P. F. Lee, M. Misiek, and K. E. Price, J. Med. Chem.,14, 770 (1971).

    Google Scholar 

  18. H. Breuer, U. D. Trenner, H. J. Schneider, M. G. Young, and H. I. Basch, J. Antibiot.,31, 546 (1978).

    Google Scholar 

  19. B. Weltzel, E. Woitun, R. Maier, W. Reuter, and U. Lechner, J. Antibiot.,38, 740 (1985).

    Google Scholar 

  20. F. Kavanagh, Analyt. Microbiol., New York: Acad. Press, 1 (1972).

    Google Scholar 

  21. Difco Manual. Nineth edition. Difco Lab. Detroit, Michigan, U.S.A., 203 (1966).

Download references

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Research Group for Antibiotics of the Hungarian Academy of Sciences, H-4010 Debrecen, P.O. Box 70, Hungary. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1524–1535, November, 1998.

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Sztaricskai, F., Batta, G., Dinya, Z. et al. Synthesis of cephalosporins carrying isoxazolyl acetamido and related side chains. Chem Heterocycl Compd 34, 1296–1307 (1998). https://doi.org/10.1007/BF02256810

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  • DOI: https://doi.org/10.1007/BF02256810

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