Solid-phase synthesis of bis-2-imidazolidinethiones from resin-bound tripeptides

Organic Letters

Volumn 2, Issue 21, 2000, Pages 3349-3350

  Nefzi, Adel ^a   Giulianotti, Marc A ^a   Ong, Nhi A ^a   Houghten, Richard A ^a  

^a TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; OLIGOPEPTIDE;

ARTICLE; CHEMISTRY; SYNTHESIS;

IMIDAZOLES; OLIGOPEPTIDES;

EID: 0034687176     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000225e     Document Type: Article

References (15)

1. (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
2. (b) Fruchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17.
3. (c) Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449.
4. Breakthrough of the year. Science 1998, 282, 2156-2161.
5. Ren, J.; Diprose, J.; Warren, J.; Esnouf, R. M.; Bird, L. E.; Ikemizu, S.; Slater, M.; Milton, J.; Balzarini, J.; Stuart, D. I.; Stammers, D. K. J. Biol. Chem. 2000, 275, 5633.
6. Dziadulewicz, E. K.; Ritchie, T. J.; Hallett, A.; Snell, C. R.; Ko, S. Y.; Wrigglesworth, R.; Hughes, G. A.; Dunstan, A. R.; Bloomfield, G. C.; Drake, G. S.; Brown, M. C.; Lee, W.; Burgess, G. M.; Davis, C.; Yaqoob M.; Perkins, M. N.; Campbell, E. A.; Davis, A. J.; Rang, H. P. J. Med. Chem. 2000, 43, 769.
7. Kappe, C. O. Bioorg. Med. Chem. Lett. 2000, 10, 49.
8. (a) Merrifield, R. B.; J. Am. Chem. Soc. 1963, 85, 2149.
9. (b) Merrifield, R. B. Science 1986, 232, 341.
10. For the reducton of amides in the solid-support, see: (a) Ostresh, J. M.; Schoner, C. C.; Hamashin, V. T.; Nefzi, A.; Meyer, J.-P.; Houghten, R. A. J. Org. Chem. 1998, 63, 8622.
11. (b) Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Tetrahedron 1999, 55, 35.
12. (a) Nefzi, A.; Ostresh. J. M.; Giulianotti, M.; Houghten, R. A. J. Comb. Chem. 1999, 1, 195.
13. (b) Nefzi, A.; Ostresh, J. M.; Meyer, J.-P.; Houghten, R. A. Tetrahedron Lett. 1997, 38, 931.
14. Houghten, R. A.; Pinilla, C.; Appel, J. R.; Blondelle, S. E.; Dooley, C. T.; Eichler, J.; Nefzi, A.; Ostresh, J. M. J. Med Chem. 1999, 42, 3743.
15. Ostresh, J. M.; Husar, G. M.; Blondelle, S. E.; Dorner, B.; Weber, P. A.; Houghten, R. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 11138.