Conformationally rigid N-acyl-5-alkyl-L-prolyl-pyrrolidines as prolyl oligopeptidase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 17, 2003, Pages 3611-3619

  Wallén, Erik A A ^a,c   Christiaans, Johannes A M ^a,d   Saarinen, Taija J ^a,e   Jarho, Elina M ^a   Forsberg, Markus M ^a   Venäläinen, Jarkko I ^a   Männistö, Pekka T ^a,b   Gynther, Jukka ^a,b  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b Finncovery Ltd   (Finland)

^c VU UNIVERSITY AMSTERDAM   (Netherlands)

^d Altana Pharma bv   (Netherlands)

^e ORION CORPORATION   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 BENZOYLPYRROLIDINE 1 CARBONYL)BENZOYL 5 TERT BUTYLPROLYLPYRROLIDINE; 4 PHENYLBUTANOYL 5 TERT BUTYLPROLYL 2 (HYDROXYACETYL)PYRROLIDINE; 4 PHENYLBUTANOYL 5 TERT BUTYLPROLYLPYRROLIDINE; AMIDE; METHYL GROUP; N ACYLPROLYLPYRROLIDINE; PROLINE DERIVATIVE; PROLYL ENDOPEPTIDASE; PYRROLIDINE DERIVATIVE; SUAM 1221; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; CONTROLLED STUDY; HUMAN; NONHUMAN;

EID: 0042121586     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00363-8     Document Type: Article

References (31)

1. Cunningham D.F., O'Connor B. Biochim. Biophys. Acta. 1343:1997;160.
2. Huston J.P., Hasenöhrl R.U. Behav. Brain. Res. 66:1995;117.
3. Kowall N.W., Beal M.F., Busciglio J., Duffy L.K., Yankner B.A. Proc. Natl. Acad. Sci. U.S.A. 88:1991;7247.
4. Laitinen K.S.M., van Groen T., Tanila H., Venäläinen J., Männistö P.T., Alafuzoff I. Neuroreport. 12:2001;3309.
5. Jiang C.H., Tsien J.Z., Schultz P.G., Hu Y. Proc. Natl. Acad. Sci. U.S.A. 98:2000;1930.
6. Rampon C., Jiang C.H., Dong H., Tang Y.P., Lockhart D.J., Schultz P.G., Tsien J.Z., Hu Y. Proc. Natl. Acad. Sci. U.S.A. 97:2000;12880.
7. Miura N., Shibata S., Watanabe S. Neurosci. Lett. 196:1995;128.
8. Toide K., Fujiwara T., Iwamoto Y., Shinoda M., Okamiya K., Kato T. Naunyn-Schmied. Arch. Pharmacol. 353:1996;355.
9. Yoshimoto T., Kado K., Matsubara F., Koriyama N., Kaneto H., Tsuru D. J. Pharmacobio-Dyn. 10:1987;730.
10. Atack J.R., Suman-Chauhan N., Dawson G., Kulagowski J.J. Eur. J. Pharmacol. 205:1991;157.
11. Schneider J.S., Giardiniere M., Morain P. Neuropsychopharmacology. 26:2002;176.
12. Vendeville S., Goossens F., Debreu-Fontaine M.-A., Landry V., Davioud-Charvet E., Grellier P., Scharpé S., Sergheraert C. Bioorg. Med. Chem. 10:2002;1719.
13. De Nanteuil G., Portevin B., Lepagnol J. Drugs Future. 23:1998;167.
14. Saito M., Hashimoto M., Kawaguchi N., Shibata H., Fukami H., Tanaka T., Higuchi N. J. Enzyme Inhibit. 5:1991;51.
15. Arai H., Nishioka H., Niwa S., Yamanaka T., Tanaka Y., Yoshinaga K., Kobayashi N., Miura N., Ikeda Y. Chem. Pharm. Bull. 41:1993;1583.
16. Portevin B., Benoist A., Rémond G., Hervé Y., Vincent M., Lepagnol J., De Nanteuil G. J. Med. Chem. 39:1996;2379.
17. Beausoleil E., Lubell W.D. J. Am. Chem. Soc. 118:1996;12902.
18. Beausoleil E., L'Archevêque B., Bélec L., Atfani M., Lubell W.D. J. Org. Chem. 61:1996;9447.
19. Halab L., Lubell W.D. J. Org. Chem. 64:1999;3312.
20. Bélec L., Slaninova J., Lubell W.D. J. Med. Chem. 43:2000;1448.
21. Halab L., Bélec L., Lubell W.C. Tetrahedron. 57:2001;6439.
22. Rapoport H., Sim T.B. J. Org. Chem. 64:1999;2532.
23. Ho T.L., Gopalan B., Nestor J.J. Jr. J. Org. Chem. 51:1986;2405.
24. Collado I., Ezquerra J., Pedregal C. J. Org. Chem. 60:1995;5011.
25. Wallén E.A.A., Christiaans J.A.M., Gynther J., Vepsäläinen J. Tetrahedron Lett. 44:2003;2081.
26. Wallén E.A.A., Christiaans J.A.M., Saario S.M., Forsberg M.M., Venäläinen J.I., Paso H.M., Männistö P.T., Gynther J. Bioorg. Med. Chem. 10:2002;2199.
27. Wallén, E. A. A.; Christiaans, J. A. M.; Jarho, E. M.; Forsberg, M. M.; Venäläinen, J. I.; Männistö, P. T.; Gynther, J. J. Med. Chem. In press.
28. Venäläinen J.I., Juvonen R.O., Forsberg M.M., Garcia-Horsman A., Poso A., Wallén E.A.A., Gynther J., Männistö P.T. Biochem. Pharmacol. 64:2002;463.
29. Wallén E.A.A., Christiaans J.A.M., Forsberg M.M., Venäläinen J.I., Männistö P.T., Gynther J. J. Med. Chem. 45:2002;4581.
30. Copeland R.A. Enzymes. A Practical Introduction to Structure, Mechanism and Data Analysis. 2000;Wiley, New York.
31. Gutheil W.G., Bachovchin W.W. Biochemistry. 32:1993;8723.