Macrocyclic inhibitors of penicillopepsin. 3. Design, synthesis and evaluation of an inhibitor bridged between P2 and P1'

Journal of the American Chemical Society

Volumn 120, Issue 19, 1998, Pages 4622-4628

  Smith, Whitney W ^a   Bartlett, Paul A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ACID; BIPHENYL; CARBONYL DERIVATIVE; CATION; ESTER DERIVATIVE; ETHYLENE DERIVATIVE; FLUORENE DERIVATIVE; METHANE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CYCLIZATION; ELECTROCHEMICAL ANALYSIS; ELECTRON TRANSPORT; PH; THEORY;

EID: 0032550658     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973713z     Document Type: Article

References (35)

1. Meyer, J. H.; Bartlett, P. A. J. Am. Chem. Soc. 1998, 120, 4600.
2. Ding, J.; Fraser, M.; Meyer, J. H.; Bartlett, P. A.; James, M. N. G. J. Am. Chem. Soc. 1998, 120, 4610.
3. Blundell, T. L.; Sibanda, B. L.; Hemmings, A.; Foundling, S. F.; Tickle, I. J.; Pearl, L. H.; Wood, S. P. In Molecular Graphics and Drug Design; Burgen, A. S. V., Roberts, G. C. K., Tute, M. S., Eds.; Elsevier Science Publishers BV: Amsterdam, 1986; pp 321-334.
4. Fraser, M. E.; Strynadka, N. C. J.; Bartlett, P. A.; Hanson, J. E.; James, M. N. G. Biochemistry 1992, 31, 5201.
5. Lauri, G.; Bartlett, P. A. J. Comput.-Aided Mol. Des. 1994, 8, 51.
6. O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353.
7. Li, W.; Ewing, W.; Harris, B.; Joullie, M. J. Am. Chem. Soc. 1990, 112, 7659.
8. Evans, D. A.; Bender, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506.
9. Evans, D. A.; Morrissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1985, 107, 4346.
10. Davis, F. A.; Stringer, O. D. J. Org. Chem. 1982, 47, 1774.
11. Hirschmann, R.; Yager, K. M.; Taylor, C. M.; Moore, W.; Sprengeler, P. A.; Witherington, J.; Phillips, B. W.; Smith, A. B., III J. Am. Chem. Soc. 1995, 117, 6370.
12. Oleksyszyn, J.; Subotkowska, L.; Mastalerz, P. Synth. Commun. 1979, 985. Kafarski, P.; Leijczak, B.; Szewczyk, J. Can. J. Chem. 1983, 61, 2425.
13. Oleksyszyn, J.; Subotkowska, L.; Mastalerz, P. Synth. Commun. 1979, 985. Kafarski, P.; Leijczak, B.; Szewczyk, J. Can. J. Chem. 1983, 61, 2425.
14. Bartlett, P. A.; Hanson, J. E.; Giannousis, P. P. J. Org. Chem. 1990, 55, 6268.
15. Deprotection of the side chain functionality and macrocyclization were evaluated at two points in this sequence, prior to and after introduction of the Iva-Val group. The cyclization itself proceeded in lower yield when carried out at the earlier stage, and it was difficult to acylate the macrocycle (H in place of Iva-Val in 22) without racemization.
16. McKenna, C. E.; Higa, M. T.; Cheung, N. H.; McKenna, M. Tetrahedron Lett. 1977, 155.
17. Gray, M. D. M.; Smith, D. J. H. Tetrahedron Lett. 1980, 21, 859.
18. Saady, M.; Lebeau, L.; Mioskowski, C. J. Org. Chem. 1995, 60, 2946.
19. Morrison, J. F.; Walsh, C. T. Adv. Enzymol. Relat. Areas Mol. Biol. 1987, 61, 201.
20. Henderson, P. J. F. Biochem. J. 1972, 127, 321.
21. Sefler, A. M.; Lauri, G.; Bartlett, P. A. Int. J. Pept. Protein Res. 1996, 48, 129.
22. Bistrov, V. F. Prog. NMR Spectrosc. 1976, 10, 41.
23. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. Still, W. C.; Tempczyk, A.; Hawly, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127.
24. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. Still, W. C.; Tempczyk, A.; Hawly, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127.
25. Merz, K. M., Jr.; Kollman, P. A. J. Am. Chem. Soc. 1989, 111, 5649.
26. Ferguson, D. M.; Kollman, P. A. J. Comput. Chem. 1991, 12, 620.
27. Lauri, G.; Bartlett, P. A. J. Comput.-Aided Mol. Des. 1994, 8, 51.
28. The "energy" of a cluster is considered to be that of the lowest energy single conformation contained within it.
29. Go, N.; Scheraga, H. A. Macromolecules 1970, 3, 178. Guarnieri, F.; Cui, W.; Wilson, S. R. J. Chem. Soc., Chem. Commun. 1991, 1542.
30. Go, N.; Scheraga, H. A. Macromolecules 1970, 3, 178. Guarnieri, F.; Cui, W.; Wilson, S. R. J. Chem. Soc., Chem. Commun. 1991, 1542.
31. Andrews, P. R.; Craik, D. J.; Martin, J. L. J. Med. Chem. 1984, 27, 1648. Gerhard, U.; Searle, M. S.; Williams, D. H. Bioorg. Med. Chem. Lett. 1993, 3, 803. Williams, D. H.; Searle, M. S.; Mackay, J. P.; Gerhard, U.; Maplestone, R. A. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 1172.
32. Andrews, P. R.; Craik, D. J.; Martin, J. L. J. Med. Chem. 1984, 27, 1648. Gerhard, U.; Searle, M. S.; Williams, D. H. Bioorg. Med. Chem. Lett. 1993, 3, 803. Williams, D. H.; Searle, M. S.; Mackay, J. P.; Gerhard, U.; Maplestone, R. A. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 1172.
33. Andrews, P. R.; Craik, D. J.; Martin, J. L. J. Med. Chem. 1984, 27, 1648. Gerhard, U.; Searle, M. S.; Williams, D. H. Bioorg. Med. Chem. Lett. 1993, 3, 803. Williams, D. H.; Searle, M. S.; Mackay, J. P.; Gerhard, U.; Maplestone, R. A. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 1172.
34. See footnote 18 in ref 1.
35. Hanson, J. E.; Kaplan, A. P.; Bartlett, P. A. Biochemistry 1989, 28, 6294.