Synthesis and in vitro characterization of new growth hormone secretagogues derived from ipamorelin with dipeptidomimetic N-terminals

European Journal of Medicinal Chemistry

Volumn 34, Issue 5, 1999, Pages 363-380

  Peschke, Bernd ^a   Ankersen, Michael ^a   Sehested Hansen, Birgit ^a   Kruse Hansen, Thomas ^a   Langeland Johansen, Nils ^a   Lau, Jesper ^a   Madsen, Kjeld ^a   Petersen, Hans ^a   Thøgersen, Henning ^a   Watson, Brett ^a  

^a NOVO NORDISK A S   (Denmark)

Author keywords

Constrained amino acid; GHRP 2; GHRP 6; Growth hormone secretagogue; Ipamorelin; MK677; Peptidomimetic

Indexed keywords

AMINO ACID; DIPEPTIDE; GROWTH HORMONE;

AMINO TERMINAL SEQUENCE; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; HORMONE ACTION; HORMONE STRUCTURE; HORMONE SYNTHESIS;

EID: 0032727858     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(99)80086-5     Document Type: Article

References (36)

1. Salomon F., Cuneo R.C., Hesp R., Sonksen P.H. N. Engl. J. M. 323:1989;1797-1803.
2. de Boer H., Blok G.J., Voerman H.J., Phillips M., Schouten J.A. Metabolism. 43:1994;199-203.
3. Rosen T., Eden S., Larson G., Wilhelmsen L., Bengtsson B.A. Acta Endocrinol. (Copenh.). 129:1998;195-200.
4. Merimee T.J. Laron Z. Growth Hormone, IGF-I and Growth-New Views of Old Concepts. 1997;Freund Publishing House Ltd., London, Tel Aviv.
5. Nargund R.P., van der Ploeg L.H.T. Bristo J.A. Annual Reports in Medicinal Chemistry. 1997;221-230 Academic Press, San Diego.
6. Smith R.G., van der Ploeg L.H.T., Howard A.D., Feighner S.D., Cheng K., Hickey G.J., et al. Endocr. Rev. 18:1997;621-645.
7. Momany F.A., Bowers C.Y., Reynolds G.A., Hong A., Newlander K. Endocrinology. 114:1984;1531-1536.
8. Bowers C.Y., Momany F.A., Reynolds G.A., Hong A. Endocrinology. 114:1984;1537-1545.
9. Howard A.D., Feighner S.D., Cully D.F., Arena J.P., Liberator P.A., Rosenblum C.I., et al. Science. 273:1996;974-977.
10. Pong S.S., Chaung L.Y.P., Dean D.C., Nargund R.P., Patchett A.A., Smith R.G. Mol. Endocrinol. 10:1996;57-61.
11. Patchett A.A., Nargund R.P., Tata J.R., Chen M.H., Barakat K.J., Johnston D.B.R., et al. Proc. Natl. Acad. Sci. USA. 92:1995;7001-7005.
12. Leung K.H., Miller R.R., Cohn D.A., Colletti A., McGowan E., Feeney W.P., Nargund R.P., Rosegay A., Wallace A. Proceedings of the 7th International Society for the Study of Xenobiotics. 10:1996;277.
13. Bowers C.Y. J. Pediatr. Endocrinol. 6:1993;21-31.
14. Raun K., Hansen B.S., Johansen N.L., Thøgersen H., Madsen K., Ankersen M., Andersen P.H. Eur. J. Endocrinol. 139:1998;552-561.
15. Deghenghi R. Life Science. 54:1994;1321-1328.
16. Smith R.G., Cheng K., Schoen W.R., Pong S.S., Hickey G.J., Jacks T.M., et al. Science. 260:1993;1640-1643.
17. Devita R.J., Bochis R., Frontier A.J., Kotliar A., Fisher M.H., Schoen W.R., et al. J. Med. Chem. 41:1998;1716-1728.
18. Ankersen M., Johansen N.L., Madsen K., Hansen B.S., Raun K., Nielsen K.K., et al. J. Med. Chem. 41:1998;3699-3704.
19. Hansen T.K., Hansen B.S., Raun K., Kramer K., Lau J., Peschke B., et al. J. Med. Chem. 41:1998;3705-3714.
20. Peschke B., Madsen K., Hansen B.S., Johansen N.L. Bioorg. Med. Chem. Lett. 7:1997;1969-1972.
21. McDowell R.S., Elias K.A., Stanley M.S., Burdick D.J., Burnier J.P., Chan K.S., et al. Proc. Natl. Acad. Sci. USA. 92:1995;11165-11169.
22. Elias K.A., Ingle G.S., Burnier J.P., Hammonds R.G., McDowell R.S., Rawson T.E., Somers T.C., Stanley M.S., Cronin M.J. Endocrinology. 136:1995;5694-5699.
23. Hlavácek J., Král V. Collect. Czech. Chem. Commun. 57:1992;525-530.
24. Miller D.J., Moody C.J. Tetrahedron. 51:1995;10811-10843.
25. Königs W., Happe G. Chem. Ber. 35:1902;1343-1349.
26. Königs W., Happe G. Chem. Ber. 36:1903;2904-2912.
27. Palomo C., Oiarbide M., Bindi S. J. Org. Chem. 63:1998;2469-2474.
28. Bestmann H.J., Schulz H. Chem. Ber. 95:1962;2921-2927.
29. Jackson S., Degrado W., Dwivedi A., Parthasarathy A., Higely A., Krywko J., et al. J. Am. Chem. Soc. 116:1994;3220-3230.
30. Carpino L.A. J. Am. Chem. Soc. 115:1993;4397-4398.
31. Schoen W.R., Dong O., Devita R.J., Pisano J.M., Hodges P., Cheng K., et al. Bioorg. Med. Chem. Lett. 4:1994;1117-1122.
32. Marshall J.A., Xie S. J. Org. Chem. 60:1995;7230-7237.
33. Heiman M.L., Nekola M.V., Murphy W.A., Lance V.A., Coy D.H. Endocrinology. 116:1985;410-415.
34. Jones T.H. Tetrahedron Lett. 31:1990;4543-4544.
35. Britto N., Gore V.G., Mali R.S., Ranade A.C. Synthetic Commun. 19:1989;1899-1910.
36. Bodanszky M. Bodanszky A. The practice of peptide synthesis. 1994;Springer-Verlag, Berlin, Heidelberg.