Synthesis and evaluation of aziridine analogues of presqualene diphosphate as squalene synthase inhibitors

Journal of Organic Chemistry

Volumn 64, Issue 1, 1999, Pages 6-7

  Koohang, Ali ^a   Coates, Robert M ^a   Owen, David ^b   Poulter, C Dale ^b  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; PRESQUALENE DIPHOSPHATE; SQUALENE DERIVATIVE; SQUALENE SYNTHASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033534422     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981833z     Document Type: Article

References (42)

1. (a) Poulter, C. D.; Rilling, H. C. in The Biosynthesis of Isoprenoid Compounds; Porter, J. W., Spurgeon, S. L., Eds.; Wiley: New York, 1981; Vol. 1; Chapter 8.
2. (b) Poulter, C. D. Acc. Chem. Res. 1990, 23, 70.
3. (a) Biller, S. A.; Neuenschwander, K.; Ponipom, M. M.; Poulter, C. D. Current Pharmaceutical Design 1996, 2, 1.
4. (b) Sliskovic, D. R.; Picard, J. A. Emerging Drugs 1997, 2, 93.
5. (c) Rosenberg, S. H. Expert Opin. Ther. Pat. 1998, 8, 521.
6. Abe, I.; Tomesch, J. C.; Wattanasin, S.; Prestwich, G. D. Nat. Prod. Rep. 1994, 11, 279.
7. Rilling, H. C.; Epstein, W. W. J. Am. Chem. Soc. 1969, 91, 1041.
8. Levy, B. D.; Petasis, N. A.; Serhan, C. N. Nature 1997, 389, 985.
9. Sasiak, K.; Rilling, H. C. Arch. Biochem. Biophys. 1988, 260, 622.
10. (a) Jennings, S. M.; Tsay, Y. H.; Robinson, G. W. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 6038.
11. (b) Fegueur, M.; Richard, L.; Charles, A. D.; Karst, F. Curr. Genet. 1991, 20, 365.
12. Zhang, D.; Jennings, S. M.; Robinson, G. W.; Poulter, C. D. Arch. Biochem. Biophys. 1993, 304, 133.
13. (a) Poulter, C. D.; Capson, T. L.; Thompson, M. D.; Dixit, V. M.; Bard, R. S. J. Am. Chem. Soc. 1989, 111, 3734.
14. (b) Sandifer, R. M.; Thompson, M. D.; Gaughan, R. G.; Poulter, C. D. J. Am. Chem. Soc. 1982, 104, 7376.
15. Steiger, A.; Pyun, H. J.; Coates, R. M. J. Org. Chem. 1992, 57, 3444.
16. (a) Prashad, M. J. Med. Chem. 1993, 36, 2051.
17. (b) Prashad, M.; Kathawala, F. G.; Scallen, T. J. Med. Chem. 1993, 36, 1501.
18. Oehlschlager, A. D.; Singh, S. M.; Sharma, S. J. Org. Chem. 1991, 56, 3856.
19. (a) Bergstrom, J. D.; et al. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 80.
20. (b) Dufresne, C.; et al. J. Nat. Prod. 1993, 56, 1923.
21. (c) Watson, N. S.; Procopiou, P. A. Prog. Med. Chem. 1996, 33, 331.
22. (a) Biller, S. A.; Sofia, M. J.; DeLange, B.; Forster, C.; Gordon, E. M.; Harrity, T.; Rich, L. C.; Ciosek, C. P. Jr. J. Am. Chem. Soc. 1991, 113, 8522.
23. (b) Biller, S. A.; et al. In Regulation of Isopentenoid Metabolism; Nes, W. D., Parish, E. J., Trzaskos, J. M., Eds.; American Chemical Society: Washington, DC, 1992; pp 65-80.
24. Lawrence, R. M.; et al. J. Am. Chem. Soc. 1996, 118, 11668.
25. Altman, L. J.; Kowerski, R. C.; Laungani, D. R. J. Am. Chem. Soc. 1978, 100, 6174.
26. 1a Julia, M. Y. Chem. Soc. Rev. 1991, 20, 129.
27. Atkinson, R. S.; Grimshire, M. J.; Kelly, B. J. Tetrahedron 1989, 45, 2875.
28. Coates, R. M.; Stanchina, C. L.; Koohang, A. Unpublished results.
29. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 92, 6190.
30. 3N, ether, 0 °C): (a) Marshall, J. A.; Dehoff, B. S. Tetrahedron 1987, 43, 4849.
31. (b) Heathcock, C. H.; Piettre, S.; Ruggeri, R. B.; Ragan, J. A.; Kath, J. C. J. Org. Chem. 1992, 57, 2554.
32. (c) Mori, K.; Matsui, M. Tetrahedron 1970, 26, 2801.
33. (d) Marshall, J. A.; Andersen, N. H.; Hochstetler, A. R. J. Org. Chem. 1967, 32, 113.
34. (a) Davisson, V. J.; Woodside, A. B.; Poulter, C. D. Methods Enzymol. 1984, 110, 130.
35. (b) Woodside, A. B.; Huang, Z.; Poulter, C. D. Org. Synth. 1988, 66, 211.
36. (c) Davisson, V. J.; Woodside, A. B.; Neal, T. R.; Stremler, K. E.; Muehlbacher, M.; Poulter, C. D. J. Org. Chem. 1986, 51, 4768.
37. 2).
38. a values of 8.3-8.6 have been reported for alkyl-substituted aziridines: (a) O'Rourke, C. E.; Clapp, L. B.; Edwards, J. O. J. Am. Chem. Soc. 1956, 78, 2159.
39. (b) Searles, S.; Tamers, M.; Block, F.; Quarterman, L. J. Am. Chem. Soc. 1956, 78, 4917.
40. 25a-c (a) Fujimoto, Y.; Morisaki, M.; Ikekawa, N. Steroids 1974, 24, 367.
41. (b) Giner, J.-L.; Djerassi, C. J. Am. Chem. Soc. 1991, 113, 1386.
42. (c) Nes, W. D.; Guo, D.-a; Zhou, W. Arch. Biochem. Biophys. 1997, 342, 68.