Design and synthesis of a protein:farnesyltransferase inhibitor based on sugar amino acids

Tetrahedron Letters

Volumn 40, Issue 21, 1999, Pages 4103-4106

  Overkleeft, Herman S ^a   Verhelst, Steven H L ^a   Pieterman, Elsbet ^b   Meeuwenoord, Nico J ^a   Overhand, Mark ^a   Cohen, Louis H ^b   Van Der Marel, Gijs A ^a   Van Boom, Jacques H ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b TNO   (Netherlands)

Author keywords

Ferrier rearrangement; Protein:farnesyl transferase inhibitors; Sugar amino acid; Tri O acetyl glucal

Indexed keywords

AMINO ACID DERIVATIVE; PROTEIN FARNESYLTRANSFERASE INHIBITOR;

ARTICLE; DRUG ACETYLATION; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITION; NETHERLANDS;

EID: 0033591159     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00697-8     Document Type: Article

References (31)

1. [1] a) S. Clarke, Annu. Rev. Biochem. 1992, 61, 355-386;
2. b) C. L. Sawyers, C. T. Denny, Cell 1994, 77, 171-173.
3. [2] F. L. Zhang, P. J. Casey, Annu. Rev. Biochem. 1996, 65, 241-269.
4. [3] M. Barbacid, Annu. Rev. Biochem. 1987, 56, 779-827.
5. [4] a) A. R. P. M. Valentijn, G. A. Van Der Marel, L. H. Cohen, J. H. Van Boom, Synlett 1991, 663-665;
6. b) M. Overhand, E. Pieterman, L. H. Cohen, A. R. P. M. Valentijn, G. A. Van Der Marel, J. H. Van Boom, Bioorg. Med. Chem. Lett. 1997, 7, 2435-2440;
7. c) M. Overhand, H. R. Stuivenberg, E. Pieterman, L. H. Cohen, R. E. W. Van Leeuwen, A. R. P. M. Valentijn, H. S. Overkleeft, G. A. Van Der Marel, J. H. Van Boom, Bioorg. Chem. in press;
8. d) see also ref. 5c.
9. [5] a) Y. Qian, M. A. Blaskovich, M. Saleem, C. M. Seong, S. P. Wathen, A. D. Hamilton, S. M. Sebti, J. Biol. Chem. 1994, 269, 12410-12413;
10. b) J. L. Goldstein, M. S. Brown, S. J. Stradley, Y. Reiss, L. M. Gierasch, J. Biol. Chem. 1991, 266, 15575-15578;
11. c) D. M. Leonard, J. Med. Chem. 1997, 40, 2971-2990, and references therein.
12. [6] G. D. Smith, J. F. Griffin, Science 1978, 199, 1214-1216.
13. [7] F. G. De Las Heras, A. S. Felix, P. Fernandez-Resa, Tetrahedron 1983, 39, 1617-1625.
14. +].
15. [9] In this case, the overall yield is decreased due to the formation of a secondary amine during the catalytic hydrogenation of the cyanide in 9. The occurrence of self-condensation during catalytic hydrogenation of cyanides in the absence of hydrochloric acid has been reported: M. Freifelder, Catalytic hydrogenation in organic synthesis, procedures and commentary, Wiley Intersience, New York, 1988, 43-52.
16. [10] The corresponding Fmoc protected building block proved to be insoluble in water.
17. [11] A. E. J. De Nooy, A. C. Besemer, H. Van Bekkum, Synthesis 1996, 1153-1174.
18. [12] J. Hovinen, A. Guzaev, A. Azhayev, H. Lönnberg, Tetrahedron Lett. 1993, 34, 8169-8172.
19. [13] PFT activity was determined as previously reported: L. H. Cohen, A. R. P. M. Valentijn, L. Roodenburg, R. E. W. Van Leeuwen, R. H. Huisman, R. J. Lutz, G. A. Van Der Marel, J. H. Van Boom, Biochem. Pharmacol. 1995, 49, 839-845.
20. [14] Furanoid SAA building blocks: a) L. Poitout, Y. Le Merrer, J.-C. Depezay, Tetrahedron Lett. 1995, 36, 6887-6990;
21. b) M. D. Smith, D. D. Long, D. G. Marquess, T. D. W. Claridge, G. W. J. Fleet, Chem. Commun. 1998, 2039-2040;
22. c) M. D. Smith, T. D. W. Claridge, G. E. Tranter, M. S. P. Sansom, G. W. J. Fleet, Chem. Commun. 1998, 2041-2042;
23. d) D. D, Long, M. D. Smith, D. G. Marquess, T. D. W. Claridge, G. W. J. Fleet, Tetrahedron Lett. 1998, 39, 9293-9296;
24. e) J. P. McDevitt, P. T. Lansbury, Jr., J. Am. Chem. Soc. 1996, 118, 3818-3828;
25. f) T. K. Chakraborty, S. Jayaprakash, P. V. Diwan, R. Nagaraj, S. K. B. Jampani, A. C. Kumwar, J. Am. Chem. Soc. 1998, 120, 12962-12963. Pyranoid SAA building blocks:
26. g) E. Graf Von Roedern, E. Lohof, G. Hessler, M. Hoffmann, H. Kessler, J. Am. Chem. Soc. 1996, 118, 10156-10167;
27. h) A. B. Smith, III, S. Sasho, B. A. Barwis, P. Sprengeler, J. Barbosa, R. Hirschmann, B. S. Cooperman, Bioorg. Med. Chem. Lett. 1998, 8, 3133-3136;
28. i) C. M. Timmers, J. J. Turner, C, M. Ward, G. A, Van Der Marel, M. L. C. E. Kouwijzer, P. D. J. Grootenhuis, J. H. Van Boom, Chem. Eur. J. 1997, 3, 920-929;
29. j) S.-I. Nishimura, S. Nomura, K. Yamada, Chem. Commun. 1998, 617-618;
30. k) Y. Suhara, J. E. K. Hildreth, Y. Ichikawa, Tetrahedron Lett. 1996, 37, 1575-1578;
31. l) C. Müller, E. Kitas, H. P. Wessel, Chem. Commun. 1995, 2425-2426.