Design, synthesis and SAR of potent statine-based BACE-1 inhibitors: Exploration of P1 phenoxy and benzyloxy residues

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 21, 2008, Pages 9471-9486

  Bäck, Marcus ^a   Nyhlén, Jonas ^a   Kvarnström, Ingemar ^a   Appelgren, Sara ^b   Borkakoti, Neera ^b   Jansson, Katarina ^b   Lindberg, Jimmy ^b   Nyström, Susanne ^b   Hallberg, Anders ^c   Rosenquist, Åsa ^a,b   Samuelsson, Bertil ^b,d  

^a LINKÖPING UNIVERSITY   (Sweden)

^b MEDIVIR AB   (Sweden)

^c UPPSALA UNIVERSITY   (Sweden)

^d STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Alzheimer's disease; BACE 1 inhibitors; P1 modifications; Peptidomimetics

Indexed keywords

4 [[2 [3 HYDROXY 4 [3 (METHANESULFONYLMETHYLAMINO) 5 (1 PHENYLETHYLCARBAMOYL)BENZOYLAMINO] 5 PHENOXYPENTANOYLAMINO] 3 METHYLBUTYRYLAMINO]METHYL]BENZOIC ACID; 4 [[2 [5 (3,5 DIFLUOROPHENOXY) 3 HYDROXY 4 [3 (METHANESULFONYLMETHYLAMINO) 5 (1 PHENYLETHYLCARBAMOYL)BENZOYLAMINO]PENTANOYLAMINO] 3 METHYLBUTYRYLAMINO]METHYL]BENZOIC ACID; 5 [2 [5 (3,5 DIFLUOROPHENOXY) 3 HYDROXY 4 [3 (METHANESULFONYLMETHYLAMINO) 5 (1 PHENYLETHYLCARBAMOYL)BENZOYLAMINO]PENTANOYLAMINO] 3 METHYLBUTYRYLAMINO]ISOPHTHALIC ACID; 5 [2 [5 BENZYLOXY 3 HYDROXY 4 [3 (METHANESULFONYLMETHYLAMINO) 5 (1 PHENYLETHYLCARBAMOYL)BENZOYLAMINO]PENTANOYLAMINO] 3 METHYLBUTYRYLAMINO]ISOPHTHALIC ACID; BETA SECRETASE; BETA SECRETASE 1; BETA SECRETASE INHIBITOR; PEPTIDE DERIVATIVE; STATINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; NONHUMAN; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

AMINO ACIDS; AMYLOID PRECURSOR PROTEIN SECRETASES; ASPARTIC ENDOPEPTIDASES; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; HUMANS; MODELS, MOLECULAR; PEPTIDE FRAGMENTS; PROTEASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 53749088436     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.09.041     Document Type: Article

References (35)

1. Thompson L.A., Bronson J.J., and Zusi F.C. Curr. Pharm. Des. 11 (2005) 3383
2. Hills I.D., and Vacca J.P. Curr. Opin. Drug Discov. Devel. 10 (2007) 383
3. Citron M. Trends Pharmacol. Sci. 25 (2004) 92
4. Baxter W.E., and Reitz B.A. Annu. Rep. Med. Chem. 40 (2005) 35
5. Citron M. Nat. Neurosci. 5 (2002) 1055
6. Hardy J., and Selkoe D.J. Science 297 (2002) 353
7. Wolfe M.S. J. Med. Chem. 44 (2001) 2039
8. Goedert M., and Spillantini M.G. Science 314 (2006) 777
9. Citron M. Nat. Rev. Neurosci. 5 (2004) 677
10. Luo Y., Bolon B., Kahn S., Bennett B.D., Babu-Khan S., Denis P., Fan W., Kha H., Zhang J., Gong Y., Martin L., Louis J.C., Yan Q., Richards W.G., Citron M., and Vassar R. Nat. Neurosci. 4 (2001) 231
11. Roberds S.L., Anderson J., Basi G., Bienkowski M.J., Branstetter D.G., Chen K.S., Freedman S.B., Frigon N.L., Games D., Hu K., Johnson-Wood K., Kappenman K.E., Kawabe T.T., Kola I., Kuehn R., Lee M., Liu W., Motter R., Nichols N.F., Power M., Robertson D.W., Schenk D., Schoor M., Shopp G.M., Shuck M.E., Sinha S., Svensson K.A., Tatsuno G., Tintrup H., Wijsman J., Wright S., and McConlogue L. Hum. Mol. Genet. 10 (2001) 1317
12. Senior K. Lancet 357 (2001) 692
13. Willem M., Garratt A.N., Novak B., Citron M., Kaufmann S., Rittger A., DeStrooper B., Saftig P., Birchmeier C., and Haass C. Science 314 (2006) 664
14. John V., Beck J.P., Bienkowski M.J., Sinha S., and Heinrikson R.L. J. Med. Chem. 46 (2003) 4625
15. Sisodia S.S., and St George-Hyslop P.H. Nat. Rev. Neurosci. 3 (2002) 281
16. Silvestri, R. Med. Res. Rev. 2008, doi:10.1002/med.20132.
17. Hu B., Fan K.Y., Bridges K., Chopra R., Lovering F., Cole D., Zhou P., Ellingboe J., Jin G., Cowling R., and Bard J. Bioorg. Med. Chem. Lett. 14 (2004) 3457
18. Hom R.K., Fang L.Y., Mamo S., Tung J.S., Guinn A.C., Walker D.E., Davis D.L., Gailunas A.F., Thorsett E.D., Sinha S., Knops J.E., Jewett N.E., Anderson J.P., and John V. J. Med. Chem. 46 (2003) 1799
19. Ziora Z., Kasai S., Hidaka K., Nagamine A., Kimura T., Hayashi Y., and Kiso Y. Bioorg. Med. Chem. Lett. 17 (2007) 1629
20. Johansson P.-O., Chen Y.T., Belfrage A.K., Blackman M.J., Kvarnström I., Jansson K., Vrang L., Hamelink E., Hallberg A., Rosenquist A., and Samuelsson B. J. Med. Chem. 47 (2004) 3353
21. Johansson P.-O., Lindberg J., Blackman M.J., Kvarnström I., Vrang L., Hamelink E., Hallberg A., Rosenquist A., and Samuelsson B. J. Med. Chem. 48 (2005) 4400
22. Alterman M., Björsne M., Muhlman A., Classon B., Kvarnström I., Danielson H., Markgren P.O., Nillroth U., Unge T., Hallberg A., and Samuelsson B. J. Med. Chem. 41 (1998) 3782
23. Pyring D., Lindberg J., Rosenquist A., Zuccarello G., Kvarnström I., Zhang H., Vrang L., Unge T., Classon B., Hallberg A., and Samuelsson B. J. Med. Chem. 44 (2001) 3083
24. Stachel S.J., Coburn C.A., Steele T.G., Jones K.G., Loutzenhiser E.F., Gregro A.R., Rajapakse H.A., Lai M.T., Crouthamel M.C., Xu M., Tugusheva K., Lineberger J.E., Pietrak B.L., Espeseth A.S., Shi X.P., Chen-Dodson E., Holloway M.K., Munshi S., Simon A.J., Kuo L., and Vacca J.P. J. Med. Chem. 47 (2004) 6447
25. Arslan T., Abraham A.T., and Hecht S.M. Nucleosides Nucleotides 17 (1998) 515
26. Rasmussen J.R., Slinger C.J., Kordish R.J., and Newman-Evans D.D. J. Org. Chem. 46 (1981) 4843
27. Rondot B., Durand T., Girard J.P., Rossi J.C., Schio L., Khanapure S.P., and Rokach J. Tetrahedron Lett. 34 (1993) 8245
28. Rauter A.P., Figueiredo J., Ismael M., Canda T., Font J., and Figueredo M. Tetrahedron: Asymmetry 12 (2001) 1131
29. Zuccarello G., Bouzide A., Kvarnström I., Niklasson G., Svensson S.C.T., Brisander M., Danielsson H., Nillroth U., Karlen A., Hallberg A., Classon B., and Samuelsson B. J. Org. Chem. 63 (1998) 4898
30. Yanagisawa H., Kanazaki T., and Nishi T. Chem. Lett. (1989) 687
31. Muller M., Huchel U., Geyer A., and Schmidt R.R. J. Org. Chem. 64 (1999) 6190
32. Ghosh A.K., Bilcer G., Harwood C., Kawahama R., Shin D., Hussain K.A., Hong L., Loy J.A., Nguyen C., Koelsch G., Ermolieff J., and Tang J. J. Med. Chem. 44 (2001) 2865
33. Rich D.H., Sun C.Q., Vara Prasad J.V., Pathiasseril A., Toth M.V., Marshall G.R., Clare M., Mueller R.A., and Houseman K. J. Med. Chem. 34 (1991) 1222
34. Kimura T., Shuto D., Hamada Y., Igawa N., Kasai S., Liu P., Hidaka K., Hamada T., Hayashi Y., and Kiso Y. Bioorg. Med. Chem. Lett. 15 (2005) 211
35. Baldwin E.T., Bhat T.N., Gulnik S., Hosur M.V., Sowder II R.C., Cachau R.E., Collins J., Silva A.M., and Erickson J.W. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 6796