Erratum: Aminoimidazoles as potent and selective human β-secretase (BACE1) inhibitors (Journal of Medicinal Chemistry (2009) 52 (6314) DOI: 10.1021/jm9006752);Aminoimidazoles as potent and selective human β-secretase (BACE1) inhibitors

Journal of Medicinal Chemistry

Volumn 52, Issue 20, 2009, Pages 6314-6323

  Malamas, Michael S ^a   Erdei, Jim ^a   Gunawan, Iwan ^a   Barnes, Keith ^b   Johnson, Matthew ^b   Yu, Hui ^b   Turner, Jim ^a   Yun, Hu ^a   Wagner, Erik ^a   Fan, Kristi ^a   Olland, Andrea ^a   Bard, Jonathan ^a   Robichaud, Albert J ^a  

^a PFIZER INC   (United States)

^b Albany Molecular Research   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 (3 PYRIMIDIN 5 YLPHENYL) 8 [4 (TRIFLUOROMETHOXY)PHENYL] 2,3,4,8 TETRAHYDROIMIDAZO[1,5 A]PYRIMIDIN 6 AMINE; 8 [3 (2 FLUOROPYRIDIN 3 YL)PHENYL] 8 [4 (TRIFLUOROMETHOXY)PHENYL] 2,3,4,8 TETRAHYDROIMIDAZO[1,5 A]PYRIMIDIN 6 AMINE; ASPARTIC PROTEINASE; BETA SECRETASE INHIBITOR; CATHEPSIN D; IMIDAZOLE DERIVATIVE; PEPSIN A; PYRIDINE; PYRIMIDINE; RENIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL ACTIVITY; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG ACTIVITY; DRUG IDENTIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME BINDING; IC 50; MOLECULAR MODEL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

AMYLOID BETA-PEPTIDES; AMYLOID PRECURSOR PROTEIN SECRETASES; ANIMALS; ASPARTIC ACID ENDOPEPTIDASES; CHO CELLS; CRICETINAE; CRICETULUS; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; FLUORESCENCE RESONANCE ENERGY TRANSFER; HUMANS; IMIDAZOLES; INHIBITORY CONCENTRATION 50; LIGANDS; MICE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PEPTIDE FRAGMENTS; PROTEASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 70350050829     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901921x     Document Type: Erratum

References (32)

1. Selkoe, D. J. Alzheimer disease: genotypes, phenotypes, and treatments. Science 1977, 275, 630-631.
2. Hardy, J. The Alzheimer family of diseases: many etiologies, one pathogenesis? Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 2095-2097.
3. Vassar, R.; Citron, M. Aβ-generating enzymes: recent advances in β- and γ-secretase research. Neuron 2000, 27, 419-422. (Pubitemid 30951842)
4. Selkoe, D. J. Alzheimer's disease: genes, proteins, and therapy. Physiol. Rev. 2001, 81, 741-766.
5. Hussain, I.; Powell, D.; Howlett, D. R.; Tew, T. g.; Meek, T. D.; Chapman, C.; Gloger, I. S.; Murphy, K. E.; Southan, C. D.; Ryan, D. M.; Smith, T. S.; Simmons, D. L.; Walsh, F. S.; Dingwall, C.; Christie, G. Identification of a novel aspartic protease (Asp2) as β- secretase. Mol. Cell. Neurosci. 1999, 14, 419-427.
6. Lin, X.; Koelsch, G.; Wu, S.; Downs, D.; Dashti, A.; Tang, J. Human aspartic protease memapsin 2 cleaves the β-secretase site of β-amyloid precursor protein. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 1456-1460.
7. Vassar, R.; Bennett, B. D.; Babu-Khan, S.; Kahn, S.; Mendiaz, E. A.; Denis, P.; Teplow, D. B.; Ross, S.; Amarante, P.; Loeloff, R.; Luo, Y.; Fischer, S.; Fuller, J.; Edenson, S.; Lile, J.; Jarosinski, M. A.; Biere, A. L.; Curran, E.; Burgess, T.; Louis, J.-C.; Collins, F.; Treanor, J.; Rogers, G.; Citron, M. β-Secretase cleavage of Alzheimer's amyloid precursor protein by transmembrane aspartic protease BACE. Science 1999, 286, 735-741. (Pubitemid 129515714)
8. Ghosh, A.; Kumaragurubaran, N.; Tang, J. Recent developments of structure-based β-secretase inhibitor's for Alzheimer's disease. Curr. Top. Med. Chem. 2005, 5, 1609-1622.
9. Cumming, J. N.; Iserloh, U.; Kennedy, M. E. Design and development of BACE1 inhibitors. Curr. Opin. Drug Discovery Dev. 2004, 7, 536-556.
10. Durham, T. B.; Shepherd, T. A. Progress toward the discovery and development of efficacious BACE inhibitors. Curr. Opin. Drug Discovery Dev. 2006, 9, 776-791.
11. Baxter, E. W.; Reitz, A. B. BACE inhibitors for the treatment of Alzheimer's disease. Annu. Rep. Med. Chem. 2005, 40, 35-48.
12. Schmidt, B.; Baumann, S.; Braub, H. A.; Larbig, G. Inhibitors and modulators of β- and γ-secretase. Curr. Top. Med. Chem. 2006, 6, 377-392.
13. Guo, T.; Hobbs, D. W. Development of BACE1inhibitors for Alzheimer's disease. Curr. Med. Chem. 2006, 13, 1811-1829.
14. John, V.; Beck, J. P.; Bienkowski,M. J.; Sinha, S.; Heinrikson,R. l. Human β-secretase (BACE) and BACE inhibitors. J. Med. Chem. 2003, 46, 4625-4630.
15. Carmen Villaverde, M.; Gonzalez-Louro, L.; Sussman, F. The search for drug leads targeted to the β-secretase: an example of the roles of computer assisted approaches in drug discovery. Curr. Top. Med. Chem. 2007, 7, 980-990.
16. Hong, L.; Koelsch, L. X.; Wu, S.; Terzyan, S.; Ghosh, A.; Zhang, X. C.; Tang, J. Structure of the protease domain of memapsin 2 (β- secretase) complexed with inhibitor. Science 2000, 290, 150-153. (Pubitemid 30752091)
17. 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.; Vacca, J. P. Structure-based design of potent and selective cell-permeable inhibitors of human β-secretase (BACE1). J. Med. Chem. 2004, 47, 6447-6450. (Pubitemid 39657304)
18. Coburn, C. A.; Stachel, S. J.; Li, Y.-M.; Rush, D. M.; Steele, T. G.; Chen-Dodson, E.; Holloway, M. K.; Xu, M.; Huang, Q.; Lai, M.- T.; DiMuzio, J.; Crouthamel, M.-C.; Shi, X.-P.; Sardana, V.; Chen, Z.; Munshi, S.; Kuo, L.; Makara, G. M.; Annis, D. A.; Tadikonda, P. K.; Nash, H. M.; Vacca, J. P. Identification of a small molecule nonpeptide active site β-secretase inhibitor that displays a nontraditional binding mode for aspartyl proteases. J. Med. Chem. 2004, 47, 6117-6119.
19. Garino, C.; Pietrancosta, N.; Laras, Y.; Moret, V.; Rolland, A.; Quelever, G.; Kraus, J.-L. BACE1 inhibitory activities of new substituted phenyl-piperazine coupled to various heterocycles: chromene, coumarin, and quinoline. Bioorg. Med. Chem. Lett. 2006, 16, 1995-1999.
20. Huang, D.; Luthi, U.; Kolb, P.; Cecchine, M.; Barberis, A.; Caflisch, A. In silico discovery of β-secretase inhibitors. J. Am. Chem. Soc. 2006, 128, 5436-5443.
21. Huang, D.; Luthi, U.; Kolb, P.; Edler, K.; Cecchine, M.; Audedat, S.; Barberis, A.; Caflisch, A. Discovery of cell-permeable nonpeptide inhibitors of β-secretase by high-throughput docking and continuum electrostatics calculations. J. Med. Chem. 2005, 48, 5108-5111.
22. Rajapaske, H. A.; Nantermet, P. G.; Selnick, H. G.; Munshi, S.; McGaughey, G. B.; Lindsley, S. R.; Young, M. B.; Lai, M.-T.; Espeseth, A. S.; Shi, X.-P.; Colussi, D.; Pietrak, B.; Crouthamel, M.-C.; Tugusheva, K.; Huang, Q.; Simon, A. J.; Kuo, L.; Hazuda, D. J.; Graham, S.; Vacca, J. P. Discovery of oxadiazoyl tertiary carbinamine inhibitors of β-secretase (BACE1). J. Med. Chem. 2006, 49, 7270-7273.
23. Edwards, P. D.; Albert, J. S.; Sylvester, M.; Aharony, D.; Andisik, D.; Callaghan, O.; Campbell, J. B.; Carr, R. A.; Chessari, G.; Congreve, M.; Frederickson, M.; Folmer, R. H.; Geschwindner, S.; Koether, G.; Kolmodin, K.; Krumrine, J.; Mauger, R. C.; Murray, C. W.; Olsson, L.; Patel, S.; Spear, N.; Tian, G. Application of fragment-based lead generation to the discovery of novel, cyclic amidine β-secretase inhibitors with nanomolar potency, cellular activity and high ligand efficiency. J. Med. Chem. 2007, 50, 5912-5925.
24. Murray, C, W.; Callaghan, O.; Chessari, A.; Congreve, M.; Frederickson, M.; Hartshorn, M. J.; McMenamin, R.; Patel, S.; Wallis, N. Application of fragment screening by X-ray crystallography to β-secretase. J. Med. Chem. 2007, 50, 1116-1123.
25. Congreve, M.; Aharony, D.; Albert, J.; Callaghan, O.; Campbell, J.; Carr, R. A. E.; Chessari, G.; Cowan, S.; Edwards, P. D.; Frederickson, M.; McMenamin, R.; Murray, C. W.; Patel, S.; Wallis, N. Application of fragment screening by X-ray crystallography to the discovery of aminopyridines as inhibitors of β-secretase. J. Med. Chem. 2007, 50, 1124-1132.
26. Geschwindner, S.; Olsson, L.-L.; Albert, J.; Deinum, J.; Edwards, P. D.; de Beer, T.; Folmer, R. H. A. Discovery of a novel warhead against β-secretase through fragment-based lead generation. J. Med. Chem. 2007, 50, 5903-5911.
27. Cole, D. C.; Manas, E.; S.; Stock, J. R.; Condon, J. S.; Jennings, L. D.; Aulabaugh, A.; Chopra, R.; Cowling, R.; Ellingboe, J. W.; Fan, K. Y.; Harrison, B. L.; Hu, Y.; Jacobsen, S.; Jin, G.; Lin, L.; Lovering, F. E.; Malamas, M. S.; Stahl, J.; Strand, J.; Sukhedo, M. N.; Svenson, K.; Turner, M. J.; Wagner, E.; Wu, J.; Zhou, P.; Bard, J. Acylguanidines as small-molecule β-secretase inhibitors. J. Med. Chem. 2006, 49, 6158-6161.
28. Stille, J. K. The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
29. Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457-2483.
30. Wu, P.; Brand, L. Resonance energy transfer: methods and applications. Anal. Biochem. 1994, 218, 1-13.
31. McMartin, C.; Bohacek, R. S. J. Comput.-Aided Mol. Des. 1997, 11, 333-344.
32. Hsiao, K.; Chapman, P.; Nilsen, S.; Eckman, C.; Harigaya, Y.; Younkin, S.; Yang, F.; Cole, G. Correlative memory deficits, Abeta elevation, and amyloid plaques in transgenic mice. Science 1996, 274, 99-102.