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
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.
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.
Y. Nishitani, T. Aoki, T. Yoshida, and W. Nagata, J. Antibiot.,41, 316 (1988).
G. Nannini, E. Perrone, D. Severino, A. Bedeschi, G. Biasoli, G. Meinardi, and A. Bianchi, J. Antibiot.,34, 412 (1981).
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).
I. Miskolczi, F. Sztaricskai, P. Herczegh, R. Bogncr, and I. Koczka, J. Antibiot.,38, 1273 (1985).
I. Miskolczi, F. Sztaricskai, and R. Bogncr, Org. Prep. Proc. Int.,14, 233 (1982).
W. J. Wheeler, D. R. Finley, R. J. Messenger, R. Koehler, and J. T. Ott, J. Antibiot.,39, 121 (1986).
E. Nakayama, K. Fujimoto, Sh. Muramatsu, and J. Ide, J. Antibiot.,45, 1193 (1992).
A. Sala, D. Chiarino, M. Napoletano, E. Albini, A. Carenzi, and D. B. Bella, J. Antibiot.,40, 1555 (1987).
F. Nakayama, K. Watanabe, M. Miyauchi, K. Fujimoto, and J. Ide, J. Antibiot.,43, 1123 (1990).
N. K. Kochetkov, E. D. Homutova, and M. V. Bazilevskij, Zh. Obshch. Khim.,38, 2736 (1958).
A. March, Compt. Rend.,132, 698 (1901).
S. D. Sokolov and N. K. Kochetkov, Zh. Obshch. Khim.,33, 1192 (1963).
V. F. Pozdnev, Khim. Prirodn. Soed., N6, 764 (1974).
R. M. DeMarinis, J. R. E. Hoover, G. L. Dunn, P. Actor, J. V. Uri, and J. A. Weisbach, J. Antibiot.,28, 412 (1075).
W. J. Gottstein, A. H. Eachus, P. F. Misco, P. F. Lee, M. Misiek, and K. E. Price, J. Med. Chem.,14, 770 (1971).
H. Breuer, U. D. Trenner, H. J. Schneider, M. G. Young, and H. I. Basch, J. Antibiot.,31, 546 (1978).
B. Weltzel, E. Woitun, R. Maier, W. Reuter, and U. Lechner, J. Antibiot.,38, 740 (1985).
F. Kavanagh, Analyt. Microbiol., New York: Acad. Press, 1 (1972).
Difco Manual. Nineth edition. Difco Lab. Detroit, Michigan, U.S.A., 203 (1966).
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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