Synthesis and in vitro evaluation of the Ras farnesyltransferase inhibitor pepticinnamin E

Angewandte Chemie - International Edition

Volumn 37, Issue 9, 1998, Pages 1236-1239

  Hinterding, Klaus ^a   Hagenbuch, Patrizia ^a   Rétey, Janos ^a   Waldmann, Herbert ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Bioorganic chemistry; Enzyme inhibitors; Pepticinnamin E; Signal transduction

Indexed keywords

EID: 0032543144     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980518)37:9<1236::AID-ANIE1236>3.0.CO;2-F     Document Type: Article

References (30)

1. a) M. Barbacid, Annu. Rev. Biochem. 1987, 56, 779-827;
2. b) detailed description: H. Lodish, D. Baltimore, A. Berk, S. L. Zipursky, P. Matsudeira, J. Darnell, Molecular Cell Biology, 3rd ed., Freeman, New York, 1995, chap. 20;
3. c) organic synthesis and biological signal transduction: K. Hinterding, D. Alonso-Díaz, H. Waldmann, Angew. Chem. 1998, 110, 716-780: Angew. Chem. Int. Ed. 1998, 37, 688-749.
4. c) organic synthesis and biological signal transduction: K. Hinterding, D. Alonso-Díaz, H. Waldmann, Angew. Chem. 1998, 110, 716-780: Angew. Chem. Int. Ed. 1998, 37, 688-749.
5. A. Levitzki, Eur. J. Biochem. 1994, 226, 1-13.
6. J. F. Hancock, H. Paterson, C. J. Marshall, Cell 1990, 63, 133-139.
7. Reviews: a) D. M. Leonard, J. Med. Chem. 1997, 40, 2971-1990. b) S. Ayral-Kaloustian, J. S. Skotnicki, Annu. Rep. Med. Chem. 1996, 31, 171-180; c) G. L. Bolton, J. S. Sebolt-Leopold, J. C. Hodges, ibid. 1994, 29, 165-174; d) F. Tamanoi, Trends Biochem. Sci. 1993, 18, 350-353; e) R. M. J. Liskamp, Angew. Chem. 1994, 106, 313-315; Angew. Chem. Int. Ed. Engl. 1994, 33, 633-636.
8. Reviews: a) D. M. Leonard, J. Med. Chem. 1997, 40, 2971-1990. b) S. Ayral-Kaloustian, J. S. Skotnicki, Annu. Rep. Med. Chem. 1996, 31, 171-180; c) G. L. Bolton, J. S. Sebolt-Leopold, J. C. Hodges, ibid. 1994, 29, 165-174; d) F. Tamanoi, Trends Biochem. Sci. 1993, 18, 350-353; e) R. M. J. Liskamp, Angew. Chem. 1994, 106, 313-315; Angew. Chem. Int. Ed. Engl. 1994, 33, 633-636.
9. Reviews: a) D. M. Leonard, J. Med. Chem. 1997, 40, 2971-1990. b) S. Ayral-Kaloustian, J. S. Skotnicki, Annu. Rep. Med. Chem. 1996, 31, 171-180; c) G. L. Bolton, J. S. Sebolt-Leopold, J. C. Hodges, ibid. 1994, 29, 165-174; d) F. Tamanoi, Trends Biochem. Sci. 1993, 18, 350-353; e) R. M. J. Liskamp, Angew. Chem. 1994, 106, 313-315; Angew. Chem. Int. Ed. Engl. 1994, 33, 633-636.
10. Reviews: a) D. M. Leonard, J. Med. Chem. 1997, 40, 2971-1990. b) S. Ayral-Kaloustian, J. S. Skotnicki, Annu. Rep. Med. Chem. 1996, 31, 171-180; c) G. L. Bolton, J. S. Sebolt-Leopold, J. C. Hodges, ibid. 1994, 29, 165-174; d) F. Tamanoi, Trends Biochem. Sci. 1993, 18, 350-353; e) R. M. J. Liskamp, Angew. Chem. 1994, 106, 313-315; Angew. Chem. Int. Ed. Engl. 1994, 33, 633-636.
11. Reviews: a) D. M. Leonard, J. Med. Chem. 1997, 40, 2971-1990. b) S. Ayral-Kaloustian, J. S. Skotnicki, Annu. Rep. Med. Chem. 1996, 31, 171-180; c) G. L. Bolton, J. S. Sebolt-Leopold, J. C. Hodges, ibid. 1994, 29, 165-174; d) F. Tamanoi, Trends Biochem. Sci. 1993, 18, 350-353; e) R. M. J. Liskamp, Angew. Chem. 1994, 106, 313-315; Angew. Chem. Int. Ed. Engl. 1994, 33, 633-636.
12. Reviews: a) D. M. Leonard, J. Med. Chem. 1997, 40, 2971-1990. b) S. Ayral-Kaloustian, J. S. Skotnicki, Annu. Rep. Med. Chem. 1996, 31, 171-180; c) G. L. Bolton, J. S. Sebolt-Leopold, J. C. Hodges, ibid. 1994, 29, 165-174; d) F. Tamanoi, Trends Biochem. Sci. 1993, 18, 350-353; e) R. M. J. Liskamp, Angew. Chem. 1994, 106, 313-315; Angew. Chem. Int. Ed. Engl. 1994, 33, 633-636.
13. L. Sepp-Lorenzino, Z. Ma, E. Rands, N. E. Kohl, J. B. Gibbs, A. Oliff, N. Rosen, Cancer Res. 1995, 55, 5302-5309.
14. P. F. Lebowitz, J. P. Davide, G. C. Prendergast, Mol. Cell. Biol. 1995, 15, 6613-6622.
15. J. B. Gibbs, S. L. Graham, G. D. Hartman, K. S. Koblan, N. E. Kohl, C. A. Omer, A. Oliff. Curr. Opin. Chem. Biol. 1997, 1, 197-203.
16. a) J. B. Gibbs, A. Oliff, Annu. Rev. Pharmacol. Toxicol. 1997, 37, 143-166;
17. b) I. Sattler, F. Tamanoi in Molecular Biology Intelligence Unit Series (Ed.: M. H. Austin), RG Landes, Austin, 1996, pp. 95-137;
18. c) S. L. Graham, T. M. Williams, Exp. Opin. Ther. Patents 1996, 6, 1295-1304.
19. J. E. Buss, J. C. Marsters, Jr., Chem. Biol. 1995, 2, 787-791.
20. K. Shiomi, H. Yang, J. Inokoshi, D. Van der Pyl, A. Nakagawa, H. Takeshima, S. Omura, J. Antibiot. 1993, 46, 229-234.
21. N. Shigematsu, K. Hayashi, N. Kayakiri, S. Takase, M. Hashimoto, H. Tanaka, J. Org. Chem. 1993, 58, 170-175.
22. U. Schöllkopf, U. Groth, C. Deng, Angew. Chem. 1981, 93, 793-795; Angew. Chem. Int. Ed. Engl. 1981, 20, 798-800.
23. U. Schöllkopf, U. Groth, C. Deng, Angew. Chem. 1981, 93, 793-795; Angew. Chem. Int. Ed. Engl. 1981, 20, 798-800.
24. a) G. Höfle, W. Steglich, Synthesis 1972, 619-629;
25. b) J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
26. O. Mitsunobu, Synthesis 1981, 1-28.
27. [10] used as a reference sample was kindly provided by Prof. Satoshi Omura, The Kitasato Institute, Tokyo, Japan.
28. D. L. Pompliano, R. P. Gomez, N. J. Anthony, J. Am. Chem. Soc. 1992, 174, 7945-7946.
29. S. Tabor, C. C. Richardson, Proc. Natl. Acad. Sci. USA 1985, 82, 1074-1078.
30. R. Gomez, L. E. Goodman, S. K. Tripathy, E. O'Rourke, V. Manne, F. Tamanoi, Biochem. J. 1993, 289, 25-31.