A pseudopeptide incorporating the tetrahydrophthalazine nucleus, a constrained Aza analog of phenylalanine

International Journal of Peptide and Protein Research

Volumn 47, Issue 3, 1996, Pages 142-147

  Kling, Toni ^a   Mueller, Luciano ^a   Sieber McMaster, Ellen ^a   Lau, Wan F ^a   Meyers, Chester A ^a  

^a BRISTOL MYERS SQUIBB PHARMACEUTICAL RESEARCH INSTITUTE   (United States)

Author keywords

Azaamino acid; Conformational studies; Heterocycle; Nuclear magnetic resonance; peptidomimetic; Tetrahydrophthalazine

Indexed keywords

N [[(N ALANYL) 1,2,3,4 TETRAHYDRO 2 PHTHALAZINYL]CARBONYL]ALANINE; PHTHALAZINE DERIVATIVE; PSEUDOPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0029872808     PISSN: 03678377     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1996.tb01337.x     Document Type: Article

References (31)

1. Berger, J. & Weinstein, J. (1982) Eur. Pat. Appl. 0054862
2. Gray, C.J., Quibell, M., Bagett, N. & Hammerle, T. (1992) Int. J. Peptide Protein Res. 40, 351-362
3. Dutta, A.S., Furr, B.J.A., Giles, M.B. & Morley, J.S. (1976) Clin . Endorcrinol 5, 291s-298s
4. Dutta, A.S., Giles, M.B. & Williams, J.C. (1986) J. Chem. Soc., Perkin Trans. l, 1655-1663
5. Powers, C., Boone, R., Carroll, D., Gupton, B.F., Kam, C-M., Nishio, N., Sakamoto, M. & Tuhy, P.M. (1984) J. Biol Chem. 259, 4288-4289
6. Ho, T., Nestor Jr., J., McCrae, G.I. & Vickery, B. (1984) Int. J. Peptide Protein Res. 24, 79-84
7. Crim, L., Nestor J. Jr., & Wilson, C. (1988) Gen. Comp. Endocrinol. 71, 372-382
8. Dutta, A.S., Furr, B.J.A., Giles, M.B., Valaccaia, B. & Walpole, A.L. (1978) Biochem. Biopliys. Res. Commun. 81, 382-390
9. Greenlee, W.J., Thorsett, E.D., Springer, J.P. & Patchett, A.A. (1984) Biochem. Biophys. Res. Commun. 122, 791-797
10. Gante, J. (1989) Synthesis 405-413
11. Pinnen, F., Luisi, G., Lucente, G., Gavuzzo, E. & Cerrini, E. (1993) 7. Chem Soc.. Perkin. Trans. l, 819-824
12. Lecoq, A., Boussard, G. & Marraud, M. (1992) Tetrahedron Lett. 33, 5209-5212
13. Lecoq, A., Boussard, G., Marraud, M. & Aubry, A. (1993) Biopolymers 33, 1051-1059
14. Rutjes, F.P.J.T., Hiemstra, H., Moiweer, H.H. & Speckamp, W.N. (1988) Tetrahedron Lett. 29, 6975-6978
15. Wijkmans, J.C.H.M., van Boom, J.H. & BIoemhoff, W. (1993) Tetrahedron Lett. 34 7123-7126
16. Russel, J.R., Garner, C.D. & Joule, J. A. (1992) J. Cliem. Soc., Perkin Trans. l, 409-410
17. Kiso, Y., Ukawa, K. & Akita.T. (1980) J. Chem. Soc., Chem. Commun. 101-102
18. Nowick, C., Powell, N., Nguyen, T.M. & Noronha, G. (1992) J. Org. Chem. 57, 7364-7366
19. Zhu, G. & Bax, A., (1993) J. Magn. Reson., Part A 104, 353-357
20. (a) Braunschweiler, L. & Ernst, R. R., (1983) J. Magn. Reson. 53, 521-528;
21. (b) Bax, A. & Davis, D.G. (1985) J. Magn. Reson. 65, 355-360
22. (a) Kumar, A., Ernst, R.R. & Wüthrich, K. (1980) Biochem. Biophys. Res. Commun. 95, 1-6;
23. (b) Macura, S. & Ernst, R.R. (1980) Mol. Phys. 41 95-117;
24. Bodenhausen, G., Kolger, H. & Ernst, R.R. (1984) J. Magn. Reson. 58, 370-388
25. Bax, A., Ikura, M., Kay, L.E. & Zhu, G. (1991) J. Magn. Reson. 91, 174-178
26. Piotto, M., Saudek, V. & Sklenar, V. (1992) J. Biomol. NMR 2, 661-665
27. Marion, D., Ikura, M. & Bax, A. (1989) J. Magn. Reson. 84, 425-430
28. Chang, G., Guida, W.C. & Still, W.C. (1989) J. Am. Chem. Soc. 111, 4379-4386
29. Mohamadi, F., Richards, N.G., Guida, W.C., Liskamp, R., Lipton, M., Caulfied C., Chang, G., Hendrickson, T. & Still, W.C. (1990) J. Comput. Chem. 11, 440-467
30. Weiner, S.J., Kollman, P.A., Case, D.A., Singh, U.C., Ghio, C, Alagona, G., Profeta, Jr., S. & Weiner, P. (1984 ) J. Am. Chem. Soc. 106, 765-784
31. Still, W.C., Tempczyk, A., Hawley, R.C. & Hendrickson, T. (1990) J. Am. Chem. Soc. 112, 6127-6129