Monomers and Polymers from Nalidixic Acid — Synthesis, Characterization and Hydrolysis Study

  • Malay Ghosh

Abstract

Over the past few years, quinolone derivatives, in particular nalidixic acid and its structural analogues have proven themselves as potential antibacterial agents. These compounds are highly effective against gram negative bacteria in addition to their activity against gram positive organisms. The synthesis of polymeric derivatives of quinolone antibacterials and their biological activities are not available in the literature. In order to prepare safer, potential antibacterial agents, we planned to prepare macromolecules containing quinolones as pendent moieties. This paper will report the synthesis of three new monomers and polymers from nalidixic acid. Their characterization and hydrolysis study at pH 7.4 will also be described.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    M. Salton & G. D. Shockman, Eds., “β-Lactam Antibiotics — Mode of Action, New Developments, and Future Prospects,” Academic Press, New York, 1981.Google Scholar
  2. 2.
    H. Flynn, Ed., “Cephalosporins and Penicillins,” Academic Press, New York, 1972.Google Scholar
  3. 3.
    D. M. Bailey, Ed., “Annual Reports in Medicinal Chemistry,” Vol. 22, Academic Press, New York, 1987, and references cited therein.Google Scholar
  4. 4.
    L. Knorr, Ann. Chem., 236, 69 (1886).CrossRefGoogle Scholar
  5. 5.
    G. Y. Lesher, E. J. Froelich, M. D. Gruett, J. H. Bailey & R. P. Brundage, J. Med. Chem., 5, 1063 (1962).CrossRefGoogle Scholar
  6. 6.
    For a detailed account, see G. Y. Lesher, in: “Kirk-Othmer Encyclopedia of Chemical Technology,” Vol. 2, 3rd Ed., John Wiley, New York, 1978, p. 782.Google Scholar
  7. 7.
    J. T. Smith, Pharm. J., 299 (1984).Google Scholar
  8. 8.
    D. Felmingham, M. D. O’Hare, M. J. Robbins, R. A. Wall, A. H. Williams, A. W. Cremer, G. L. Ridgway & R. N. Grunberg, Drugs Exptl. Clin. Res., 11, 316 (1985).Google Scholar
  9. 9.
    D. C. Hooper & J. S. Wolfson, Antimicrob. Ag. Chemother., 28, 716 (1985).CrossRefGoogle Scholar
  10. 10.
    C. R. Smith, J. Antimicrob. Ag. Chemother., 19, 709 (1987).CrossRefGoogle Scholar
  11. 11.
    S. Hori, J. Shimada, A. Dsaito, T. Miyahara, S. Kurioka & M. Matsuda, 27th ICAAC, 30 (1987).Google Scholar
  12. 12.
    H. Tatsumi, H. Senda, S. Yatera, Y. Takemoto, M. Yamayoshi & K. Ohnishi, J. Toxicol. Sci., 3, 357 (1978).CrossRefGoogle Scholar
  13. 13.
    A. Gough, N. J. Barsoum, L. Mitchell, E. J. McGuire & F. A. de la Iglesia, Toxicol. Appl. Pharmacol., 51, 177 (1979).CrossRefGoogle Scholar
  14. 14.
    R. Albrecht, Prog. Drug Res., 21, 9 (1977).Google Scholar
  15. 15.
    T. Fujita, in “Drug Design: Fact or Fantasy,” Academic Press, London, 1984, p. 19.Google Scholar
  16. 16.
    C. E. Carraher & C. G. Gebelein, Eds., “Biological Activities of Polymers,” ACS Symposium Series, No. 186, American Chemical Society, Washington, D.C., 1982.Google Scholar
  17. 17.
    C. G. Gebelein & C. E. Carraher, Eds., “Polymeric Materials in Medication,” Plenum Publ. Corp., New York, 1985.Google Scholar
  18. 18.
    D. A. Tirrell, L. G. Donaruma & A. B. Turek, “Macromolecules as Drugs and as Carriers for Biologically Active Materials,” Annals of the New York Academy of Sciences, No. 446, New York Academy of Science, New York, 1985.Google Scholar
  19. 19.
    C. G. Gebelein, Ed., “Advances in Biomedical Polymers,” Plenum Publ. Corp., New York, 1987.Google Scholar
  20. 20.
    M. Ghosh, Polymer News, 13, 71 (1988).Google Scholar
  21. 21.
    M. Ghosh, Polym. Mater. Sci. Eng., 55, 755 (1986).Google Scholar
  22. 22.
    M. Ghosh, in: “Applied Bioactive Polymeric Materials,” C. G. Gebelein, C. E. Carraher & Van Foster, Eds., Plenum Publ. Corp., New York, 1989, p. 115.Google Scholar
  23. 23.
    M. Ghosh, J. Polymer Materials, 6, 81 (1989).Google Scholar
  24. 24.
    D. D. Perrin, W. L. F. Armarego & D. R. Perrin, “Purification of Laboratory Chemicals,” Pergamon Press, New York, 1986.Google Scholar
  25. 25.
    M. Spraul, in: “Bruker Report,” 9, 1 (1988).Google Scholar
  26. 26.
    J. C. Seehan & K. R. Henry-Logan, J. Amer. Chem. Soc, 79, 1262 (1957).CrossRefGoogle Scholar
  27. 27.
    MMX Calculation = MMZ-1977(QCPE 395) + MMPI (QCPE 318).Google Scholar
  28. 28.
    B. Singh & G. Y. Lesher, J. Hetero. Chem., 20, 491 (1983).CrossRefGoogle Scholar
  29. 29.
    K. Oka & S. Hara, Tetrahedron Lett., 2783 (1976).Google Scholar

Copyright information

© Springer Science+Business Media New York 1990

Authors and Affiliations

  • Malay Ghosh
    • 1
  1. 1.Department of Chemistry and Chemical EngineeringStevens Institute of TechnologyHobokenUSA

Personalised recommendations