Abstract
Optimization of the antibacterial activity of 4-amino trinem, obtained through chemical modification of the basicity of the amino group at position 4, has led to the identification of a very interesting compound characterized by a broad spectrum of activity includingPseudomonas aeruginosa.
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References
Z. Zhang, Zhongguo Linchuang Yaolixue Zazhi,13, No. 3, 163 (1997).
J. Parrick and L. K. Mehta, Progr. Heterocycl. Chem.,8, 66 (1996).
K. Bush, Antibiot. Chemother. (7th Ed.), F. O'Grady (ed.): Churchill Livingstone, Edinburgh, UK (1997), p. 306.
B. Tamburini, A. Perboni, T. Rossi, D. Donati, D. Andreotti, G. Gaviraghi, R. Carlesso, and C. Bismara, Eur. Pat. Appl. EP0416953 A2; Chem. Abstr.,116, 235337 (1992).
R. Di Fabio, D. Andreotti, S. Biondi, G. Gaviraghi, and T. Rossi, Bioorg. Med. Chem. Lett.,6, 2025 (1996).
D. Andreotti, S. Biondi, R. Di Fabio, D. Donati, E. Piga, and T. Rossi, Bioorg. Med. Chem. Lett.,6, 2019 (1996).
P. M. Jackson, S. M. Roberts, S. Davalli, D. Donati, C. Marchioro, A. Perboni, S. Proviera, and T. Rossi, J. Chem. Soc., Perkin Trans. I, No. 16, 2029 (1996).
R. Camerini, M. Panunzio, G. Bonanomi, D. Donati, and A. Perboni, Tetrahedron Lett.,37, 2467 (1996).
G. Gaviraghi, Eur. J. Med. Chem. (Suppl., Proceedings of the 13th International Symposium on Medicinal Chemistry, 1994),30, 67 (1995).
S. Hanessian, A. Griffin, and M. J. Rozema, Bioorg. Med. Chem. Lett.,7, 1857 (1997).
S. Hanessian, M. Rozema, G. B. Reddy, and J. F. Braganza, Bioorg. Med. Chem. Lett.,5, 2535 (1995).
S. Biondi, Anti-Infectives Recent Advances in Chemistry and Structure-Activity Relationships. P. H. Bentley and P. J. O'Hanlon (eds.), The Royal Society of Chemistry, Cambridge (1997), p. 86.
D. Andreotti, T. Rossi, G. Gaviraghi, D. Donati, C. Marchioro, E. Di Modugno, and A. Perboni, Bioorg. Med. Chem. Lett.,6, 491 (1996).
M. E. Tranquillini, G. L. Araldi, D. Donati, G. Pentassuglia, A. Pezzoli, and A. Ursini, Bioorg. Med. Chem. Lett.,6, 1683 (1996).
A. Perboni, G. Pentassuglia, D. Andreotti, and J. A. Winders, PCT Int. Appl., WO 9513278; Chem. Abstr.,123, 198515 (1995).
S. Gehanne, E. Piga, D. Andreotti, S. Biondi, and D. Pizzi, Bioorg. Med. Chem. Lett.,6, 2791 (1996).
A. Perboni, D. Donati, and G. Tarzia, Eur. Pat. Appl., EP 502468 A1; Chem. Abstr.,118, 80719 (1993).
L. I. Krimen, Org. Syn.,50, 1 (1970).
E. Perrone, M. Alpegiani, A. Bedeschi, F. Giudici, and G. Franceschi, Tetrahedron Lett.,25, 2399 (1984).
C. Battistini, C. Scarafile, M. Foglio, and G. Franceschi, Tetrahedron Lett.,25, 2395 (1984).
A. Yoshida, T. Hayashi, N. Takeda, S. Oida, and E. Ohki, Chem. Pharm. Bull.,31, 768 (1983).
P. D. Jeffrey and S. W. McCombie, J. Org. Chem.,47, 587 (1982).
Y. Sumita, H. Yamaga, and M. Sunagawa, J. Antibiot.,49, 89 (1995).
E. Modugno, R. Broggio, I. Erbetti, and J. Lowther, Antimicrob. Agents Chemother.,41, 2742 (1997).
Additional information
Medicines Research Centre, GlaxoWellcome S.p. A Via A. Fleming 4, 37100 Verona, Italy. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1553–1559, November, 1998.
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Andreotti, D., Biondi, S. & Donati, D. Synthesis and antibacterial activity of trinems bearing nitrogen derivatives at C(4). Chem Heterocycl Compd 34, 1324–1330 (1998). https://doi.org/10.1007/BF02256813
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DOI: https://doi.org/10.1007/BF02256813