Approaches to the synthesis of ureapeptoid peptidomimetics

Tetrahedron Letters

Volumn 38, Issue 30, 1997, Pages 5335-5338

  Kruijtzer, John A W ^a   Lefeber, Dirk J ^a   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; CHLOROACETONITRILE; ETHYLENEDIAMINE DERIVATIVE; PEPTIDE DERIVATIVE; PEPTIDOMIMETIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; TECHNIQUE;

EID: 0030764541     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01166-0     Document Type: Article

References (33)

1. (a) Simon, R.J.; Kania, R.S.; Zuckermann, R.N.; Huebner, V.D.; Jewell, D.A.; Banville, S.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C.K.; Spellmeyer, D.C.; Tan, R.; Frankel, A.D.; Santi, D.V.; Cohen, F.E.; Bartlett, P.A. Proc. Natl. Acad. Sci. USA, 1992, 89, 9367-9371;
2. (b) Kessler, H. Angew. Chem. Int. Ed. Engl. 1993, 32, 543-544.
3. Cho, C.Y.; Moran, E.J.; Cherry, S.R.; Stephans, J.C.; Fodor, S.P.A.; Adams, C.L.; Sundaram, A.; Jacobs, J.W.; Schultz, P.G. Science 1993, 261, 1303-1305.
4. (a) Burgess, K.; Linthicum, D.S.; Shin, H. Angew. Chem. Int. Ed. Engl. 1995, 34, 907-909; Burgess, K.; Ibarzo, J.; Linthicum, D.S.; Russell, D.H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A.J. J. Am. Chem. Soc. 1997, 119, 1556-1564;
5. (a) Burgess, K.; Linthicum, D.S.; Shin, H. Angew. Chem. Int. Ed. Engl. 1995, 34, 907-909; Burgess, K.; Ibarzo, J.; Linthicum, D.S.; Russell, D.H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A.J. J. Am. Chem. Soc. 1997, 119, 1556-1564;
6. (b) Hutchins, S.M.; Chapman, K.T. Tetrahedron Lett. 1994, 35, 4055-4058;
7. (c) Hutchins, S.M.; Chapman, K.T. Tetrahedron Lett. 1995, 36, 2583-2586;
8. (d) Kim, J-M.; Bi, Y.; Paikoff, S.J.; Schultz, P.O. Tetrahedron Lett. 1996, 37, 5305-5308.
9. (a) Barré, C.; Le Grel, P.; Robert, A.; Baudy-Floc'h, M. J. Chem. Soc. Chem. Comm. 1994, 607;
10. (b) Han, H.; Janda, K.D. J. Am. Chem. Soc. 1996, 118, 2539-2544.
11. (a) Moran, E.J.; Wilson, T.E.; Cho, C.Y.; Cherry, S.R.; Schultz, P.G. Biopolymers Peptide Science 1995, 37, 213-219;
12. (b) Sommerfield, T.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 553-554.
13. (a) Moree, W.J.; Schouten, A.; Kroon, J.; Liskamp, R.M.J. Int. J. Pept. Protein Res. 1995, 45, 501-507;
14. (b) Moree, W.J.; van der Marel, G.A.; Liskamp, R.M.J. J. Org. Chem. 1995, 60, 5157-5169;
15. (c) Genari, C.; Salom, B.; Potenza, D.; Williams, A. Angew. Chem. Int. Ed. Engl. 1994, 33, 2067-2068;
16. (d) De Bont, D.B.A.; Moree, W.J.; Liskamp, R.M.J. Bioorg. Med. Chem. 1996, 4, 667-672;
17. (e) Gude, M.; Piarulli, U.; Potenza, D.; Salom, B.; Gennari, C. Tetrahedron Lett. 1996, 47, 8589-8592;
18. (f) De Bont, D.B.A.; Dijkstra, G.D.H.; Den Hartog, J.A.J.; Liskamp, R.M.J. Bioorg. Med. Chem. Lett. 1996, 6, 3035-3040.
19. (a) Kruijtzer, J.A.W.; Liskamp, R.M.J. Tetrahedron Lett. 1995, 36, 6969-6972;
20. (b) Kruijtzer, J.A.W. Thesis 1996 Utrecht University, The Netherlands; Kruijtzer, J.A.W.; Liskamp, R.M.J. manuscript in preparation.
21. Kawamoto, I.; Endo, R.; Ishikawa, K.; Kojima, K.; Miyauchi, M.; Nakayama, E. Synlett. 1995, 575-577.
22. Yoon, N.M.; Brown, H.C. J. Am. Chem. Soc. 1968, 90, 2927-2938.
23. Satoh, T.; Suzuki, S.; Suzuki, Y.; Miyaji, Y.; Imai, Z. Tetrahedron Lett. 1969, 20, 4555-4558.
24. (a) Brown, H.C.; Heim, P. J. Org. Chem 1973, 38, 912-916;
25. (b) Brown, H.C.; Choi, Y.M.; Narasimhan, S. J. Org. Chem. 1982, 47, 3153-3163.
26. Campagna, F.; Carotti, A.; Casini, G. Tetrahedron Lett. 1977, 28, 1813-1816.
27. Heinzman, S.W.; Ganem, B. J. Am. Chem. Soc. 1982, 104, 6801-6802.
28. (a) Ravikumar, V.T. Synth. Commun. 1994, 24, 1767-1772;
29. (b) Schwoegler, E.J.; Adkins, H. J. Am. Chem. Soc. 1939, 61, 3499-3502.
30. The Glycine ureapeptoid monomer viz. N-Boc-ethylenediamine is commercially available, Fluka AG Switzerland.
31. (a) Gante, J. Chem. Ber. 1965, 98, 3334-3339;
32. (b) Majer, P.; Randad, R.S. J. Org. Chem. 1994, 59, 1937-1938.
33. Unfortunately, part of 17 cyclized to the corresponding C-terminal hydantoin which was isolated in 23% yield.