Synthesis and biological evaluation of non-polyene analogs of amphotericin B

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 24, 1997, Pages 3177-3182

  Rogers, Bruce N ^a   Selsted, Michael E ^a   Rychnovsky, Scott D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOTERICIN B; AMPHOTERICIN B DERIVATIVE; AMPHOTERICIN B METHYL ESTER; ANTIFUNGAL AGENT;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CRYPTOCOCCUS NEOFORMANS; DRUG SYNTHESIS; IN VITRO STUDY; STRUCTURE ACTIVITY RELATION;

CANDIDA ALBICANS; FILOBASIDIELLA NEOFORMANS;

EID: 0031455977     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10180-9     Document Type: Article

References (45)

1. This work is taken from the Ph.D. Dissertation of B.N.R. (1997), University of California, Irvine.
2. Macrolide Antibiotics: Chemistry, Biology, and Practice; Omura, S., Ed.; Academic Press: New York, NY, 1984.
3. Vandeputte, J.; Wachtel, J. L.; Stiller, E. T. Antibiot. Annu. 1956, 587.
4. Sarosi, G. A. Postgraduate Medicine 1990, 88, 151.
5. Gallis, H. A.; Drew, R. H.; Pickard, W. W. Rev. Infect. Dis. 1990, 12, 308.
6. Mechlinski, W.; Schaffner, C. P.; Ganis, P.; Avitabile, G. Tetrahedron Lett. 1970, 3873.
7. (a) Hammond, S. M. In Progress in Medicinal Chemistry; Ellis, G. P., West, G. B., Eds.; Elsevier: North-Holland, 1977; Vol. 14, p 106.
8. (b) Reference l, p 425.
9. (c) Brajtburg, J.; Powderly, W. G.; Kobayashi, G. S.; Medoff, G. Antimicrob. Agents Chemother. 1990, 34, 183.
10. (d) Hartsel, S; Bolard, J. Trends Pharmacol. Sciences 1996, 17, 445.
11. Bolard, J. Biochim. Biophys. Acta 1986, 864, 257.
12. Mickus, D. E.; Levitt, D. G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1992, 114, 359.
13. Langlet, J.; Berges, J.; Caillet, J.; Demaret, J.-P. Biochim. Biophys. Acta 1994, 1191, 79.
14. For recent reviews see: (a) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021.
15. (b) Beau, J. M. In Recent Prog. Chem. Synth. Antibiot.; Lukacs, G., Ohno, M., Eds.; Springer: Berlin, 1990, 135.
16. Bruzzese, T.; Cambieri, M.; Recusani, F. J. Pharm. Sci. 1975, 64, 462.
17. Jarzebski, A.; Falkowski, L.; Borowski, E. J. Antibiot. 1982, 35, 220.
18. Grzybowska, J.; Borowski, E. J. Antibiot. 1990, 43, 907.
19. Czerwinski, A.; Konig, W. A.; Zieniawa, T.; Sowinski, P.; Sinnwell, V.; Milewski, S.; Borowski, E. J. Antibiot. 1991, 44, 979.
20. Schaffner, C. P.; Borowski, E. Antibiot. Chemother. 1961, 11, 724.
21. (a) Czerwinski, A.; Grzybowska, J.; Borowski, E. J. Antibiot. 1986, 39, 1025.
22. (b) Wright, J. M.; Albarella, J. A.; Krepski, L. R.; Loebenberg, D. J. Antibiot. 1982, 35, 911.
23. Parmegaini, R. M.; Loebenberg, B.; Antonacci, B.; Yarosh-Tomaine, R.; Scupp, R.; Wright, J. J.; Chiu, P. J. S.; Miller, G. H. Antimicrob. Agents Chemother. 1987, 31, 1756.
24. Mechlinski, W.; Schaffner, C. P. J. Antibiot. 1972, 25, 256.
25. A review of much of their work appeared while our work was in progress: MacPherson, D. T.; Corbett, D. F.; Costello, B. C.; Driver, M. J.; Greenlees, A. R.; S., M. W.; Shanks, C. T.; Taylor, A. W. In Recent Advances in the Chemistry of Anti-infective Agents; Bentley, P. H., Ponsford, R., Eds.; Royal Society of Chemistry: Cambridge (UK), 1993; p 205.
26. (a) Taylor, A. W.; Costello, B. J.; Hunter, P. A.; MacLachlan, W. S.; Shanks, C. T. J. Antibiot. 1993, 46, 486.
27. (b) Taylor, A. W.; MacPherson, D. T. Tetrahedron Lett. 1994, 35, 5289.
28. (a) Costello, B. J.; Driver, M. J.; MacLachlan, W. S.; Taylor, A. W. J. Chem. Soc., Perkin Trans. 1 1993, 1829.
29. (b) MacLachlan, W. S.; Readshaw, S. A. Tetrahedron Lett. 1995, 36, 1735.
30. (a) Driver, M. J.; Greenlees, A. R.; MacLachlan, W. S.; MacPherson, D. T.; Taylor, A. W. Tetrahedron Lett. 1992, 33, 4357.
31. (b) Driver, M. J.; Greenlees, A. R.; MacPherson, D. T. J. Chem. Soc., Perkin Trans. 1 1992, 3155.
32. (c) Corbett, D. F.; Dean, D. K.; Greenlees, A. R.; Macpherson, D. T. J. Antibiot. 1995, 48, 509.
33. For a review of these trials see: Hoeprich, P. D.; Flynn, N. M.; Kawachi, M. M.; Lee, K. K.; Lawrence, R. M.; Heath, L. K.; Schaffner, C. P. Ann. N. Y. Acad. Sci.: Antifungal Drugs 1988, 544, 517.
34. Hoeprich, P. D. Clinical Infectious Diseases (Suppl. 1) 1992, 14, S114.
35. Nicolaou, K. C.; Chakraborty, T. K.; Ogawa, Y.; Daines, R. A.; Simpkins, N. S.; Furst, G. T. J. Am. Chem. Soc. 1988, 110, 4660.
36. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
37. (a) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138.
38. (b) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813.
39. The necessary spacers were prepared by palladium catalyzed stannylation of diiodo-p-terphenyl. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
40. Rano, T. A.; Greenlee, M. L., DiNinno, F. P., Lee, W., Rouen, G. P. Poster presented at the IV International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994.
41. Alred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
42. 2 and sp Carbon Centers. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: London, 1991; Vol. 3, p 521.
43. Austin, W. B.; Bilow, N.; Kelleghan, W. J.; Lau, K. S. Y. J. Org. Chem. 1981, 46, 2280.
44. (a) Lehrer, R. I.; Rosenman, M.; Harwig, S. S. S. L.; Jackson, R.; Eisenhauer, P. J. Immunolgical Methods 1991, 137, 167.
45. (b) Van Abel, R. J.; Tang, Y.-Q.; Rao, V. S. V.; Dobbs, C. H.; Tran, D.; Barany, G.; Selsted, M. E. Int. J. Peptide Protein Res. 1995, 45, 401.