A small chemical library of 2-aminoimidazole derivatives as BACE-1 inhibitors: Structure-based design, synthesis, and biological evaluation

European Journal of Medicinal Chemistry

Volumn 48, Issue , 2012, Pages 206-213

  Chiriano, Gianpaolo ^a,b   De Simone, Angela ^c   Mancini, Francesca ^c   Perez, Daniel I ^d   Cavalli, Andrea ^b,c   Bolognesi, Maria Laura ^c   Legname, Giuseppe ^a   Martinez, Ana ^d   Andrisano, Vincenza ^c   Carloni, Paolo ^e   Roberti, Marinella ^c  

^a SISSA   (Italy)

^b ISTITUTO ITALIANO DI TECNOLOGIA   (Italy)

^c UNIVERSITY OF BOLOGNA   (Italy)

^d INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^e German Research School for Simulation Sciences GmbH   (Germany)

Author keywords

2 Aminoimidazole; Alzheimer's disease; Amyloid beta peptide; Drug design; Hit identification

Indexed keywords

1 (2 CHLOROBENZYL) 4 [4 (DIBENZO[B,D]FURAN 1 YL)BENZYL] 1H IMIDAZOL 2 AMINE; 1 (3,5 DIFLUOROBENZYL) 4 [(3',5' DIMETHOXYBIPHENYL 3 YL)METHYL] 1H IMIDAZOL 2 AMINE; 1 (3,5 DIFLUOROBENZYL) 4 [(3',5' DIMETHOXYBIPHENYL 4 YL)METHYL] 1H IMIDAZOL 2 AMINE; 1 (3,5 DIFLUOROBENZYL) 4 [[3' (BENZYLOXY)BIPHENYL 4 YL]METHYL] 1H IMIDAZOL 2 AMINE; 1 (3,5 DIFLUOROBENZYL) 4 [[4' (TRIFLUOROMETHYL)BIPHENYL 4 YL]METHYL] 1H IMIDAZOL 2 AMINE; 1 (4 FLUOROBENZYL) 4 [(3',5' DIMETHOXYBIPHENYL 3 YL)METHYL] 1H IMIDAZOL 2 AMINE; 1 (4 FLUOROBENZYL) 4 [(3',5' DIMETHOXYBIPHENYL 4 YL)METHYL] 1H IMIDAZOL 2 AMINE; 2 AMINOIMIDAZOLE DERIVATIVE; 2 BROMO 3 (3',5' DIMETHOXYBIPHENYL 4 YL)PROPANAL; 4 BENZYL 1 (2 CHLOROBENZYL) 1H IMIDAZOL 2 AMINE; 4 BENZYL 1 (3,5 DIFLUOROBENZYL) 1H IMIDAZOL 2 AMINE; 4 BENZYL 1 (4 FLUOROBENZYL) 1H IMIDAZOL 2 AMINE; BETA SECRETASE INHIBITOR; IMIDAZOLE DERIVATIVE; METHYL 3 (3',5' DIMETHOXYBIPHENYL 4 YL)PROPANOATE; UNCLASSIFIED DRUG;

ARTICLE; ARTIFICIAL MEMBRANE; BLOOD BRAIN BARRIER; CELL ASSAY; CONTROLLED STUDY; DRUG DESIGN; DRUG DETERMINATION; DRUG PENETRATION; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ASSAY; MICROWAVE COOKING; STRUCTURE ACTIVITY RELATION;

ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; AMYLOID PRECURSOR PROTEIN SECRETASES; ANIMALS; CELL SURVIVAL; CHICKENS; HUMANS; IMIDAZOLES; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NEURONS; SMALL MOLECULE LIBRARIES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84855983969     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.12.016     Document Type: Article

References (34)

1. D.J. Selkoe Nature 399 1999 A23 A31
2. C. Haass, and D.J. Selkoe Nat. Rev. Mol. Cell. Biol. 8 2007 101 112
3. M. Citron Nat. Rev. Drug Discov. 9 2010 387 398
4. M. Bartolini, and V. Andrisano ChemBioChem 11 2010 1018 1035
5. M.L. Bolognesi, R. Matera, A. Minarini, M. Rosini, and C. Melchiorre Curr. Opin. Chem. Biol. 13 2009 303 308
6. F. Panza, V. Solfrizzi, V. Frisardi, C. Capurso, A. D'Introno, A.M. Colacicco, G. Vendemiale, A. Capurso, and B.P. Imbimbo Drugs Aging 26 2009 537 555
7. R.J. Kelleher, and J. Shen Science 330 2010 1055 1056
8. M.K. Holloway, P. Hunt, and G.B. McGaughey Drug Dev. Res. 70 2009 70 93
9. L. Hong, G. Koelsch, X. Lin, S. Wu, S. Terzyan, A.K. Ghosh, X.C. Zhang, and J. Tang Science 290 2000 150 153
10. L. Hong, R.T. Turner, G. Koelsch, D. Shin, A.K. Ghosh, and J. Tang Biochemistry 41 2002 10963 10967
11. Huang Wen-Hai, Sheng Rong, and H. Yong-Zhou Curr. Med. Chem. 16 2009 1806 1820
12. R. Silvestri Med. Res. Rev. 29 2009 295 338
13. X. Luo, and R. Yan Int. J. Clin. Exp. Pathol. 3 2010 618 628
14. G. Chiriano, A. Sartini, F. Mancini, V. Andrisano, M.L. Bolognesi, M. Roberti, M. Recanatini, P. Carloni, and A. Cavalli Chem. Biol. Drug Des. 77 2011 268 271
15. M. Haniu, P. Denis, Y. Young, E.A. Mendiaz, J. Fuller, J.O. Hui, B.D. Bennett, S. Kahn, S. Ross, T. Burgess, V. Katta, G. Rogers, R. Vassar, and M. Citron J. Biol. Chem. 275 2000 21099 21106
16. J.D. Sullivan, R.L. Giles, and R.E. Looper Curr. Bioact. Compd. 5 2009 39 78
17. D.S. Ermolat'ev, J.B. Bariwal, H.P.L. Steenackers, S.C.J. De Keersmaecker, and E.V. Van der Eycken Angew. Chem. Int. Ed. Engl. 49 2010 9465 9468
18. D.S. Ermolat'ev, E.V. Babaev, and E.V. Van der Eycken Org. Lett. 8 2006 5781 5784
19. H.P. Steenackers, D.S. Ermolat'ev, B. Savaliya, A.D. Weerdt, D.D. Coster, A. Shah, E.V. Van der Eycken, D.E. De Vos, J. Vanderleyden, and S.C. De Keersmaecker J. Med. Chem. 54 2011 472 484
20. P. Camps, X. Formosa, C. Galdeano, D. Muñoz-Torrero, L. Ramírez, E. Gómez, N. Isambert, R. Lavilla, A. Badia, M.V. Clos, M. Bartolini, F. Mancini, V. Andrisano, M.P. Arce, M.I. Rodríguez-Franco, Ó Huertas, T. Dafni, and F.J. Luque J. Med. Chem. 52 2009 5365 5379
21. S. Czvitkovich, S. Duller, E. Mathiesen, K. Lorenzoni, B. Imbimbo, B. Hutter-Paier, M. Windisch, and R. Wronski J. Mol. Neurosci. 43 2010 257 267
22. W.K. Hagmann J. Med. Chem. 51 2008 4359 4369
23. L. Hong, and J. Tang Biochemistry 43 2004 4689 4695
24. S.J. Stachel, C.A. Coburn, D. Rush, K.L.G. Jones, H. Zhu, H. Rajapakse, S.L. Graham, A. Simon, M. Katharine Holloway, T.J. Allison, S.K. Munshi, A.S. Espeseth, P. Zuck, D. Colussi, A. Wolfe, B.L. Pietrak, M.-T. Lai, and J.P. Vacca Bioorg. Med. Chem. Lett. 19 2009 2977 2980
25. I.D. Hills, M.K. Holloway, P. de León, A. Nomland, H. Zhu, H. Rajapakse, T.J. Allison, S.K. Munshi, D. Colussi, B.L. Pietrak, D. Toolan, S.J. Haugabook, S.L. Graham, and S.J. Stachel Bioorg. Med. Chem. Lett. 19 2009 4993 4995
26. L. Di, E.H. Kerns, K. Fan, O.J. McConnell, and G.T. Carter Eur. J. Med. Chem. 38 2003 223 232
27. L.K. Chico, L.J. Van Eldik, and D.M. Watterson Nat. Rev. Drug Discov. 8 2009 892 909
28. W.M. Pardridge Alzheimers Dement. 5 2009 427 432
29. M.S. Malamas, J. Erdei, I. Gunawan, K. Barnes, M. Johnson, Y. Hui, J. Turner, Y. Hu, E. Wagner, K. Fan, A. Olland, J. Bard, and A.J. Robichaud J. Med. Chem. 52 2009 6314 6323
30. J. Wang, P. Cieplak, and P.A. Kollman J. Comput. Chem. 21 2000 1049 1074
31. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E., Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N.J. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian Inc., Wallingford CT, 2009.
32. G. Jones, P. Willett, R.C. Glen, A.R. Leach, and R. Taylor J. Mol. Biol. 267 1997 727 748
33. G. Bottegoni, A. Cavalli, and M. Recanatini J. Chem. Inf. Model. 46 2006 852 862
34. G. Bottegoni, W. Rocchia, M. Recanatini, and A. Cavalli Bioinformatics 22 2006 e58 e65