Design, synthesis and in vitro evaluation of pyridinium ion based cyclase inhibitors and antifungal agents

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 1, 1996, Pages 97-103

  Rose, Ingo C ^a   Sharpe, Bradley A ^a   Lee, Roger C ^a   Griffin, John H ^a   Capobianco, John O ^b   Zakula, Dorothy ^b   Goldman, Robert C ^b  

^a STANFORD UNIVERSITY   (United States)

^b ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOTERICIN B; ANTIFUNGAL AGENT; ENZYME INHIBITOR; OXIDOSQUALENE CYCLASE; OXIDOSQUALENE CYCLASE INHIBITOR; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; STEROL SYNTHESIS; STRUCTURE ACTIVITY RELATION;

EID: 0029937885     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(95)00177-8     Document Type: Article

References (42)

1. Abe, I.; Rohmer, M.; Prestwich, G. D. Chem Rev. 1993, 93, 2189.
2. Buntel, C. J.; Griffin, J. H. J. Am. Chem Soc. 1992, 114, 9711.
3. (a) Corey, E. J.; Matsuda, S. P. T.; Bartel, B. Proc. Natl. Acad. Sci. U.S.A. 1994, 97, 2211.
4. (b) Shi, Z.; Buntel, C. J.; Griffin, J. H. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7370.
5. Ochs, D.; Kaletta, C.; Entian, K.-D.; Beck-Sickinger, A.; Poralla, K. J. Bacteriol. 1992, 174, 298.
6. Corey, E. J.; Matsuda, S.; Bartel, B. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 11628.
7. Reipen, I. G; Poralla, K.; Sahm, H.; Sprenger, G. A. Microbiology 1995, 141, 155.
8. (a) Kusano, M.; Shibuya, M.; Sankawa, U.; Ebizuka, Y. Biol. Pharm. Bull. 1995, 18, 195.
9. (b) Abe, I.; Prestwich, G. D., Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 9274.
10. Baker, C. H.; Matsuda, S. P. T.; Liu, D. R.; Corey, E. J. Biochem. Biophys. Res. Comm. 1995, 213, 154.
11. Buntel, C. J.; Griffin, J. H. In Isopentenoids and Other Natural Products: Evolution and Function; Nes, W.D., Ed.; ACS Symp. Series 562; American Chemical Society: Washington, DC, 1994; pp 44-54.
12. Others have concluded that conserved tryptophan residues are important to cyclase structure/function based on the finding that they are often found in repetitive 'QW motifs'. See (a) Poralla, K.; Hewelt, A.; Prestwich, G. D.; Abe, I.; Reipen, I.; Sprenger, G. Trends Biochem. Sci. 1994, 157.
13. (b) Poralla, K. Bioorg. Med. Chem. Lett. 1994, 4, 285.
14. Dougherty, D. A., Stauffer, D. A. Science 1990, 250, 1558.
15. McCurdy, A., Jimenez, L., Stauffer, D. A., Dougherty, D. A. J. Am. Chem Soc. 1992, 114, 10314.
16. van Tamelen, E. E. J. Am. Chem Soc. 1982, 104, 6480.
17. Cornforth, J. W. Angew. Chem. 1968, 7, 903.
18. (a) Johnson, W. S.; Telfer, S. J.; Cheng, S.; Schubert, U. J. Am. Chem Soc. 1987, 109, 2517.
19. (b) Johnson, W. S.; Lindell, S. D.; Steele, J. J. Am. Chem Soc. 1987, 109, 5852.
20. Johnson, W. S. Tetrahedron 1991, 47, xi.
21. (d) Johnson, W.S.; Buchanan, R. A.; Bartlett, W. R.; Tham, F. S.; Kullnig, R. K. J. Am. Chem Soc. 1993, 115, 504.
22. Benveniste, P. Annu. Rev. Plant Physiol. 1986, 37, 275.
23. For a review of recent work with inhibitors of sterol biosynthesis, including inhibitors of (oxido)squalene cyclase enzymes, see: Abe, I.; Tomesch, J. C.; Wattanasin, S.; Prestwich, G. D. Nat. Prod. Rep. 1994, 11, 279.
24. Corey, E. J. ; Ortiz de Montellano, P. R.; Lin, K.; Dean, P. D. G. J. Am. Chem Soc. 1967, 89, 2797.
25. (a) Duriatti, A.; Bouvier-Navé, P.; Benveniste, P.; Schuber, F.; Delprino, L.; Balliano, G.; Cattel, L. Biochem. Pharmacol. 1985, 34, 2765.
26. (b) Cattel, L.; Ceruti, M.; Viola, F.; Delprino, L.; Balliano, G.; Duriatti, A.; Bouvier-Navé, P. Lipids 1986, 27, 31.
27. Ryder, N. S.; Dupont, M.-C.; Frank, I. FEBS Lett. 1986, 204, 239.
28. Mercer, E. I.; Morris, P. K.; Baldwin, B. C. Comp. Biochem. Physiol. B 1985, 80, 341.
29. (a) Taton, M.; Benveniste, P.; Rahier, A. Biochem. Biophys. Res. Comm. 1986, 138, 764.
30. (b) Taton, M.; Benveniste, P.; Rahier, A.; Johnson, W. S.; Liu, H.; Sudhakar, A. R. Biochemistry 1992, 31, 7892.
31. (a) Dodd, D. S.; Oehlschlager, A. C. J. Org. Chem. 1992, 57, 2794.
32. (b) Dodd, D. S.; Oehlschlager, A. C.; Georgopapadakou, N. H.; Polak, A.-M.; Hartman, P. G. J. Org. Chem. 1992, 57, 7226.
33. (a) Jolidon, S.; Polak, A.-M.; Guerry, P.; Hartman, P. G. Biochem. Soc. Trans. 1990, 18, 47.
34. (b) Jolidon, S.; Polak-Wyss, A.; Hartman, P. G.; Guerry, P. In Recent Advances in the Chemistry of Anti-Infective Agents', Bentley, P. H., Ponsford, R., Eds.; Thomas Graham House: Cambridge, 1993; pp 223-233.
35. Cotlier, E.; Sanders, D.; Wyhinny, G. Opthalmic Res. 1974, 6, 107.
36. Hugo, W. B. In Surface Activity and the Microbial Cell; SCI Monograph No. 19; Society of Chemical Industry: London, 1965; pp 67-82.
37. Hiom, S. J.; Furr, J. R.; Rüssel, A. D.; Dickinson, J. R. Microbios 1993, 74, 111.
38. LoCicero et al. found that the antifungal activity of n-alkylpyridinium ions towards Sclerotinia fructicola, Venturia inaequalis, Alternaria oleracea, and Phytophythora infestans was greatest with tetradecylpydridinium ion and decreased with either shortening or lengthening of the n-alkyl chain. See LoCicero, J. C.; Frear, D. E. H.; Miller, H. J. J. Biol. Chem. 1948, 172, 689.
39. Goldman, R. C.; Zakula, D.; Capobianco, J. O.; Sharpe, B. A.; Griffin, J. H. Antimicrob. Agents Chemother., in press.
40. Coates, R. M.; Ley, D. A.; Cavender, P. L. J. Org. Chem. 1978, 43, 4915.
41. Capobianco, J. O.; Doran, C. C.; Goldman, R. C.; De, B. J. Antimicrob. Chemother. 1992, 30, 781.
42. Kato, T.; Kawase, Y. Agricult. Biol. Chem. 1976, 40, 2379.