An introduction of a pyridine group into the structure of prolyl oligopeptidase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 21, 2006, Pages 5590-5593

  Jarho, Elina M ^a   Venäläinen, Jarkko I ^a   Juntunen, Juha ^a   Yli Kokko, A Leena ^a   Vepsäläinen, Jouko ^a   Christiaans, Johannes A M ^a   Forsberg, Markus M ^a   Järvinen, Tomi ^a   Männistö, Pekka T ^a   Wallén, Erik A A ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

Inhibitor; Prolyl oligopeptidase; Pyridine

Indexed keywords

PROLINE; PROLINE DERIVATIVE; PROLYL ENDOPEPTIDASE INHIBITOR; PYRIDINE; PYRIDINE DERIVATIVE; WATER;

ARTICLE; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; LIPOPHILICITY; PROTEIN STRUCTURE;

ENZYME INHIBITORS; HUMANS; PYRIDINES; SERINE ENDOPEPTIDASES;

EID: 33748776070     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.08.029     Document Type: Article

References (30)

1. Toide K., Iwamoto Y., Fujiwara T., and Abe H. J. Pharmacol. Exp. Ther. 274 (1995) 1370
2. Shishido Y., Furushiro M., Tanabe S., Taniguchi A., Hashimoto S., Yokokura T., Shibata S., Yamamoto T., and Watanabe S. Pharm. Res. 15 (1998) 1907
3. Shishido Y., Furushiro M., Tanabe S., Nishiyama S., Hashimoto S., Ohno M., Yamamoto T., and Watanabe S. Pharmacol. Biochem. Behav. 55 (1996) 333
4. Shishido Y., Furushiro M., Tanabe S., Shibata S., Hashimoto S., and Yokokura T. Eur. J. Pharmacol. 372 (1999) 135
5. Schneider J.S., Giardiniere M., and Morain P. Neuropsychopharmacology 26 (2002) 176
6. Morain P., Robin J.L., De Nanteuil G., Jochemsen R., Heidet V., and Guez D. Br. J. Clin. Pharmacol. 50 (2000) 350
7. Jiang C.H., Tsien J.Z., Schultz P.G., and Hu Y. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 1930
8. Roßner S., Schulz I., Zeitschel U., Schliebs R., Bigl V., and Demuth H.U. Neurochem. Res. 30 (2005) 695
9. Schulz I., Gerhartz B., Neubauer A., Holloschi A., Heiser U., Hafner M., and Demuth H.U. Eur. J. Biochem. 269 (2002) 5813
10. Williams R.S., Eames M., Ryves W.J., Viggars J., and Harwood A.J. EMBO J. 18 (1999) 2734
11. Schulz I., Zeitschel U., Rudolph T., Ruiz-Carrillo D., Rahfeld J.U., Gerhartz B., Bigl V., Demuth H.U., and Roßner S. J. Neurochem. 94 (2005) 970
12. Jarho E.M., Venäläinen J.I., Huuskonen J., Christiaans J.A.M., Garcia-Horsman J.A., Forsberg M.M., Järvinen T., Gynther J., Männistö P.T., and Wallén E.A.A. J. Med. Chem. 47 (2004) 5605
13. Wallén E.A.A., Christiaans J.A.M., Saarinen T.J., Jarho E.M., Forsberg M.M., Venäläinen J.I., Männistö P.T., and Gynther J. Bioorg. Med. Chem. 11 (2003) 3611
14. Dressman J.B., Berardi R.R., Dermentzoglou L.C., Russell T.L., Schmaltz S.P., Barnett J.L., and Jarvenpaa K.M. Pharm. Res. 7 (1990) 756
15. Tsutsumi S., Okonogi T., Shibahara S., Ohuchi S., Hatsushiba E., Patchett A.A., and Christensen B.G. J. Med. Chem. 37 (1994) 3492
16. Nakajima T., Ono Y., Kato A., Maeda J., and Ohe T. Neurosci. Lett. 141 (1992) 156
17. Saito M., Hashimoto M., Kawaguchi N., Shibata H., Fukami H., Tanaka T., and Higuchi N. J. Enzyme Inhib. 5 (1991) 51
18. Tsuda M., Muraoka Y., Nagai M., Aoyagi T., and Takeuchi T. J. Antibiot. 49 (1996) 909
19. Tsuda M., Muraoka Y., Nagai M., Aoyagi T., and Takeuchi T. J. Antibiot. 49 (1996) 1022
20. Tsuru D., Yoshimoto T., Koriyama N., and Furukawa S. J. Biochem. 104 (1988) 580
21. Vendeville S., Goossens F., Debreu-Fontaine M.A., Landry V., Davioud-Charvet E., Grellier P., Scharpe S., and Sergheraert C. Bioorg. Med. Chem. 10 (2002) 1719
22. Beausoleil E., L'Archevêque B., Bélec L., Atfani M., and Lubell W.D. J. Org. Chem. 61 (1996) 9447
23. Sim T.B., and Rapoport H. J. Org. Chem. 64 (1999) 2532
24. Menghin S., Pertz H.H., Kramer K., Seifert R., Schunack W., and Elz S. J. Med. Chem. 46 (2003) 5458
25. In the synthesis of 4-pyridin-3-yl-butyronitrile, NaCN was used instead of KCN and no purification was needed after evaporation of DMSO. In the work-up of 4-pyridin-3-yl-butyric acid, the reaction mixture was washed with DCM before the adjustment of pH and after continuous extraction of the product no further purification was needed.
26. Pardridge W. NeuroRx 2 (2005) 3
27. Tute, M. S. Lipophilicity in Drug Action and Toxicology; 1st ed.; Pliska, V., Testa, B., van de Waterbeemd, H. Eds.; VCH: Weinheim, 1996; p 7.
28. Venäläinen J.I., Juvonen R.O., Forsberg M.M., Garcia-Horsman J.A., Poso A., Wallén E.A.A., Gynther J., and Männistö P.T. Biochem. Pharmacol. 64 (2002) 463
29. Atack J.R., Suman-Chauhan N., Dawson G., and Kulagowski J.J. Eur. J. Pharmacol. 205 (1991) 157
30. Lipinski C.A. J. Pharmacol. Toxicol. Methods 44 (2000) 235