Solid-phase and combinatorial synthesis in β-lactam chemistry

Current Pharmaceutical Design

Volumn 5, Issue 11, 1999, Pages 955-964

  Mata, Ernesto G ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM ANTIBIOTIC;

CHIRALITY; COUPLING FACTOR; DRUG EFFICACY; DRUG SYNTHESIS; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OLIGOMERIZATION; PHOTOLYSIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REVIEW; SOLID PHASE EXTRACTION;

BETA-LACTAMS; COMBINATORIAL CHEMISTRY TECHNIQUES; STEREOISOMERISM;

EID: 0032701759     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (39)

1. a) Jung, G.; Beck-Sickinger, A.G. Angew. Chem. Int. Ed. Engl., 1992, 31, 367.
2. b) Peptides and Nonpeptides Libraries - A Handbook; Jung, G. Ed.; VCH: Berlin, 1996.
3. Bunin, B.A.; Ellman, J.A. J. Am. Chem. Soc., 1992, 114, 10997.
4. For recent reviews in Combinatorial Chemistry, see: a) Gallop, M.A.; Barrett, R.W.; Dower, W.J.; Fodor, S.P.A.; Gordon, E.M. J. Med. Chem., 1994, 37, 1233.
5. b) Gordon, E.M.; Barrett, R.W.; Dower, W.J.; Fodor, S.P.A.; Gallop, M.A. J. Med. Chem., 1994, 37, 1386.
6. c) Terrett, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron, 1995, 57, 8135.
7. d) Balkenhohl, F.; Bussche-Hünnefeld, Ch.; Lansky, A.; Zechel, Ch. Angew. Chem. Int. Ed. Engl., 1996, 35, 2288.
8. e) Furlán, R.L.E.; Labadie, G.R.; Pellegrinet, S.C.; Ponzo, V.L. Química Nova, 1996, 19, 411.
9. f) Lowe, G. Chemical Society Reviews 1995, 24, 309-317.
10. g) Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555-600.
11. h) Patel, D.V.; Gordon, E.M. Drug Discovery Today 1996, 1, 134-144.
12. i) Special Issue Acc. Chem. Res. 1996, 29, No. 3.
13. j) A Practical Guide to Combinatorial Chemistry, DeWitt, S.H; Czarnik, A.W., Eds., ACS Books: Washington, 1997.
14. k) The Combinatorial Index, Bunin, B.A., Academic Press: San Diego, 1998.
15. l) Combinatorial Chemistry and Molecular Diversity in Drug Discovery, Gordon, E.M.; Kerwin, J.F., Eds., Wiley & Sons: New York, 1998.
16. For a review on combinatorial approaches to lactam rings, see: Pitlik, J. Curr. Opin. Drug Disc. Develop., 1998, 1 , 51.
17. Ruhland, B.; Bhandari, A.; Gordon, E.M.; Gallop, M.A. J. Am. Chem. Soc., 1996, 118, 253.
18. Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P. Tetrahedron Lett., 1988, 29, 4005.
19. Rapp, W. In Reference 1b, page 425.
20. Holmes, C.P.; Jones, D.G. J. Org. Chem., 1995, 60, 2318.
21. Fitch, W.L.; Detre, G.; Holmes, C.P.; Shoolery, J.N.; Keifer, P.A. J. Org. Chem., 1994, 59, 7955.
22. Keifer, P.A. J. Org. Chem., 1996, 61, 1558.
23. Ruhland, B.; Bombrun, A.; Gallop, M.A. J. Org. Chem., 1997, 62, 7820.
24. Singh, R.; Nuss, J.M. Tetrahedron Lett., 1999, 40, 1251.
25. Mitchell, A.R.; Kent, S.B.H.; Engelhard, M.; Merrifield, R.B. J. Org. Chem., 1978, 43, 2845.
26. Pei, Y.; Houghten, R.A.; Kiely, J.S. Tetrahedron Lett., 1997, 38, 3349.
27. Han, H.; Wolfe, M.M.; Brenner, S.; Janda, K.D. Proc. Natl. Acad. Sci. USA, 1995, 92, 6419.
28. Zhao, X.; Metz, W.A.; Sieber, F.; Janda, K.D. Tetrahedron Lett., 1998, 39, 8433.
29. Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett., 1998, 39, 1257.
30. Boger, D.L.; Chai, W.; Jin, Q. J. Am. Chem. Soc., 1998, 120, 7220; and references cited therein.
31. Pitlik, J.; Townsend, C.A. Bioorg. Med. Chem. Lett., 1997, 7, 3129.
32. Armstrong, R.W.; Brown, S.D.; Keating, T.A.; Tempest, P.A. In Combinatorial Chemistry. Synthesis and Application; Wilson, S.R., Czarnik, A.W., Eds.; John Wiley &Sons: New York, 1997; page 153.
33. Furka, A.; Sebestyén, F.; Asgedom, M.; Dibo, G. Int. J. Peptide Protein Res., 1991, 37, 487.
34. Bose, A.K.; Manhas, M.S.; Mathur, A.; Wagle, D.R. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer-Verlag: Berlin, 1993; Vol. 2, page 551.
35. Mata, E.G. Tetrahedron Lett., 1997, 38, 6335.
36. Pátek, M.; Drake, B.; Lebl, M. Tetrahedron Lett., 1995, 36, 2227.
37. Delpiccolo, C.M.L.; Mata, E.G. Tetrahedron Lett., submitted.
38. Furman, B.; Thürmer, R; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem. Int. Ed., 1999, 38, 1121.
39. Kaluza, Z.; Park, S.H. Synlett, 1996, 895.