Solid and solution phase combinatorial synthesis of ureas

Tetrahedron Letters

Volumn 39, Issue 42, 1998, Pages 7811-7814

  Nieuwenhuijzen, José W ^a   Conti, Paolo G M ^b   Ottenheijm, Harry C J ^b   Linders, Joannes T M ^b  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b NV ORGANON   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

TACHYKININ RECEPTOR; UREA;

AMINO ACID ANALYSIS; AMINO ACID SEQUENCE; ARTICLE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PURIFICATION; SOLID PHASE EXTRACTION; SYNTHESIS;

EID: 0032532249     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01708-0     Document Type: Article

References (20)

1. 1 (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E.M. J. Med Chem. 1994, 37, 1233.
2. (b) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med Chem. 1994, 37, 1385.
3. (c) Desai, M. C.; Zuckerman, R. N.; Moos, W. H. Drug Dev. Res. 1994, 33, 174.
4. (d) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135.
5. (f) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 555.
6. (g) Patel, D. V.; Gordon, E. M. Drug Disc. Today 1996, 1, 134.
7. (h) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996 52, 4527;
8. (i) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643.
9. 2 Hellberg, S.; Eriksson, L.; Jonsson, J.; Lindgren, F.; Sjostrom, M.; Skagerberg, B.; Wold, S.; Andrews, P. Int. J. Pept. Protein Res. 1991, 37, 414.
10. 3 Boden, P.; Eden, J. M.; Hodgson, J.; Horwell, D. C.; Hughes, J.; McKnight, A. T.; Lewthwaite, R. A.; Pritchard, M. C.; Raphy, J.; Meecham, K.; Ratcliffe, G. S.; Suman-Chauchan, N.; Woodruff, G. N. J. Med. Chem. 1996, 39, 1664.
11. 4 (a) Lam, P. Y. S. Science, 1994, 263, 380.
12. (b) Kempf, D. J.: Marsh, K. C.; Paul, D. A.; Knigge, M. F.; Norbeck, D. W.; Kohlbrenner, W. E.; Codacovi, L.; Vasavanonda, S.; Bryant, P.; Wang, X. C.; Wideburg, N. E.; Clement, J. J.; Plattner, J. J.; Erickson, J. W. Antimicrob. Agents Chemother. 1991, 35, 2209.
13. (c) Geteman, D. P.; DeCrescenzo, G. A.; Henitz, R. M.; Reed, K. L.; Talley, J. J.; Bryant, M. L.; Clare, M.; Houseman, K. A.; Marr, R. R.; Mueller, R. A.; Vazquez, M. L.; Shien, H. S.; Sallings, W. C.; Stegeman, R. A. J. Med. Chem. 1993, 36, 288.
14. (d) Norwick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A. J. Am. Chem. Soc. 1995, 117, 89.
15. 5 Katritzky, A. R.; Pleynet, D. P. M.; Yang, B. J. Org. Chem. 1997, 62, 4155.
16. 6 Recently, Burgess et al. reported the solid phase synthesis of oligoureas based on the reaction of an isocyanate with an amine. 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 and references therein.
17. 7 Hutchins and Chapman have reported the solid phase synthesis of ureas derived from glutamic acid, which was attached to the resin with the side-chain carboxylate. Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055.
18. 13C-NMR: δ 27.31 (q), 38.63 (t), 52.30 (d), 53.88 (q), 54.17 (q), 62.56 (t), 127.02 (d), 128.53 (d), 129.44 (d), 136.06 (s), 156.73 (s), 172.09 (s), 173.03 (s).
19. 2 (2×). The filtrate and washings were collected in pre-weighed tubes and concentrated to give the desired urea 10.
20. 1H and TOCSY). The products 10 were analysed by MS and HPLC.