Rapid synthesis of matrix metalloproteinase inhibitors via Ugi four-component condensation

Synlett

Volumn , Issue 6, 1998, Pages 637-639

  Floyd, Christopher D ^a   Harriett, Laura A ^a   Miller, Andrew ^a   Patel, Sanjay ^a   Saroglou, Lydia ^a   Whittaker, Mark ^a  

^a British Biotech Pharmaceuticals Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 13844313713     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1729     Document Type: Article

References (32)

1. a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288;
2. b) Floyd, C. D.; Lewis, C. N.; Whittaker, M. Chem. Br. 1996, 32, 31;
3. c) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135.
4. a) Gordeev, M. F.; Patel, D. V.; Gordon, E. M. J. Org. Chem. 1996, 61, 924:
5. b) Wipf, R.; Cunningham, A. Tetrahedron Lett. 1995, 36, 7819:
6. c) Obst, U.; Gramlich, V.; Diederich, F.; Weber, L.; Banner, D. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 1739.
7. a) Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810;
8. b) Ugi, I.; Lohberger, S.; Karl, R. The Passerini and Ugi Reactions. In Comprehensive Organic Synthesis Vol. 2 (2); Trost, B. M.; Fleming, I.; Heathcock, C. H. Eds.; Pergamon Press: Oxford, 1991; pp. 1083-1109.
9. Ugi, I. Proc. Estonian Acad. Sci. Chem. 1995, 44, 237.
10. a) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123;
11. b) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1995, 117, 7842;
12. c) Keating, T. A.; Armstrong, R. W. Idem, J. Am. Chem. Soc. Ibid 1996, 118, 2574;
13. d) Tempest, P. A.; Brown, S. D.; Armstrong, R. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 640;
14. e) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149.
15. Sutherlin, D. P.; Stark, T. M.; Hughes, R.; Armstrong, R. J. Am. Chem. Soc. 1995, 117, 7842.
16. Cao, X.; Moran, E. J.; Siev, D.; Lio, A.; Ohashi, C.; Mjalli, A. M. M. Bioorg. Med. Chem. Lett. 1995, 5, 2953.
17. a) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M . M. Tetrahedron Lett. 1996, 37, 751;
18. b) Mjalli, A. M. M.; Sarshar, S.; Baiga, T. J. Tetrahedron Lett. 1996, 37, 2943.
19. a) Beckett, R. P.; Davidson, A. H.; Drummond, A. H.; Huxley, P.; Whittaker, M. Drug Discovery Today 1996, 1, 16;
20. b) Morphy, J. R.; Millican, T. A.; Porter, J. R. Curr. Med. Chem. 1995, 2, 743.
21. Chiral succinate derivatives 2 were prepared using the Evans' chiral auxiliary in a procedure developed by Crimmin and co-workers:- Beckett, R. P.; Crimmin, M. J.; Davis, M. H.; Spavold, Z. Synlett 1993, 137.
22. Wachter, E.; Werhahn, R. First experiences with four-component-condensation as a tool for peptide attachment to solid supports. In Solid Phase Methods in Protein Sequence Analysis, INSERM Symposium No. 5; Previero, A.; Coletti-Previero, M.-A. Éds.; Elsevier: Amsterdam, 1977; pp. 185-192.
23. Rink, H. Tetrahedron Lett. 1987, 28, 3787.
24. Fernando, A.; Kneib-Cordonier, N.; Biancalana, S.; Gera, L.; Masada, R. I.; Hudson, D.; Barany, G. J. Org. Chem. 1990, 55, 3730.
25. Ugi, I.; Steinbrückner, C. Chem. Ber. 1961, 94, 2802
26. Ugi, I. Intra-Sci. Chem. Rep. 1971, 5, 229.
27. Waki, M.; Meienhofer, J. J. Am. Chem. Soc. 1977, 99, 6075.
28. 2 +ve) δ 175.8(+), 175.5(+), 175.4(+), 175.2(+), 170.8(+), 170.5(+), 142.5(+), 142.4(+), 128.8(-), 128.7(-), 128.7(-), 128.7(-), 126.1 (-), 61.2(-), 61.1(-). 49.1(-), 48.9(-), 43.2(-), 42.2(-), 38.1(+), 37.2(+), 36.0(+), 35.9(+), 35.3(+), 35.0(+), 33.4(+), 33.1(+), 32.9(+), 32.9(+), 32.5(+), 29.7(+). 29.5(+), 27.2(-), 27.0(-), 25.9(+), 25.2(+); ESMS M+1 431.2.
29. a) Schöllkopf, U.; Böhme, P. Angew. Chem., Int. Ed. Engl. 1971, 10, 491;
30. b) Gassman, P. G.; Greraban, R. S. Tetrahedron Lett. 1984, 25, 3259.
31. 50 value of 60 nM). The preparation and biological evaluation of the more potent hydroxamates will be reported elsewhere.
32. The preparation of 1,1′-iminodicarboxylic acid based ACE inhibitors by a modified Ugi reaction has been recently reported: Demharter, A.; Horl, W.; Herdtweck, E.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1996, 35, 173.