BACE1 inhibitory activities of enantiomerically pure, variously substituted N-(3-(4-benzhydrylpiperazin-1-yl)-2-hydroxypropyl) arylsulfonamides

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 22, 2010, Pages 7991-7996

  Bertini, Simone ^a   Ghilardi, Elisa ^a   Asso, Valentina ^a   Granchi, Carlotta ^a   Minutolo, Filippo ^a   Pineschi, Mauro ^a   Di Bussolo, Valeria ^a   Bortolato, Andrea ^b   Moro, Stefano ^b   Saba, Alessandro ^a   MacChia, Marco ^a  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

Alzheimer; BACE1; Benzhydryl piperazines; Docking; Enzyme inhibition

Indexed keywords

BETA SECRETASE 1; PIPERAZINE DERIVATIVE;

ALZHEIMER DISEASE; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENZYME INHIBITION; STEREOCHEMISTRY;

ALZHEIMER DISEASE; AMYLOID PRECURSOR PROTEIN SECRETASES; BINDING SITES; CATALYTIC DOMAIN; COMPUTER SIMULATION; HUMANS; HYDROGEN BONDING; PROTEASE INHIBITORS; STEREOISOMERISM; SULFONAMIDES;

EID: 78449234521     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.09.032     Document Type: Article

References (24)

1. G.G. Glenner, and C.W. Wong Biochem. Biophys. Res. Commun. 120 1984 885
2. C. Ballatore, V.M.-Y. Lee, and J.Q. Trojanowski Nat. Rev. Neurosci. 8 2007 663
3. M.S. Forman, J.Q. Trojanowski, and V.M.-Y. Lee Nat. Med. 10 2004 1055
4. S.L. Roberds, J. Anderson, G. Basi, M.J. Bienkowski, D.G. Branstetter, K.S. Chen, S. Freedman, N.L. Frigon, D. Games, K. Hu, K. Johnson-Wood, K.E. Kappenman, T. Kawabe, I. Kola, R. Kuehn, M. Lee, W. Liu, R. Motter, N.F. Nichols, M. Power, D.W. Robertson, D. Schenk, M. Schoor, G.M. Shopp, M.E. Shuck, S. Sihna, K.A. Svensson, G. Tatsuno, H. Tintrup, J. Wijsman, S. Wright, and L. McConlogue Hum. Mol. Genet. 10 2001 1317
5. V. John, J.P. Beck, M.J. Bienkowski, S. Sinha, and R.L. Heinrikson J. Med. Chem. 46 2003 4625
6. Some recent examples are reported in: J.C. Barrow, K.E. Rittle, P.L. Ngo, H.G. Selnick, S.L. Graham, S.M. Pitzenberger, G.B. McGaughey, D. Colussi, M.-T. Lai, Q. Huang, K. Tugusheva, A.S. Espeseth, A.J. Simon, S.K. Munshi, and J.P. Vacca ChemMedChem 2 2007 995
7. M.C. Maillard, R.K. Hom, T.E. Benson, J.B. Moon, S. Mamo, M. Bienkowski, A.G. Tomasselli, D.D. Woods, D.B. Prince, D.J. Paddock, T.L. Emmons, J.A. Tucker, M.S. Dappen, L. Brogley, E.D. Thorsett, N. Jewett, S. Sinha, and V. John J. Med. Chem. 50 2007 776
8. BACE-inhibition assays have been carried out as reported in: L. Magnoni, G.C. Terstappen, and W. Fecke Assay Drug Dev. Technol. 3 2005 287
9. QikProp, version 3.0, Schrödinger, LLC, New York, NY, 2007.
10. J.M. Luco J. Chem. Inf. Comput. Sci. 39 1999 396
11. J. Kelder, P.D. Grootenhuis, D.M. Bayada, L.P. Delbressine, and J.P. Ploemen Pharm. Res. 16 1999 1514
12. Ajay, G.W. Bemis, and M.A. Murkco J. Med. Chem. 42 1999 4942
13. T. Fujimoto, Y. Matsushita, H. Gouda, N. Yamaotsu, and S. Girono Bioorg. Med. Chem. Lett. 18 2008 2771
14. Schrödinger Suite 2007 Induced Fit Docking protocol; Glide version 4.5, Schrödinger, LLC, New York, NY, 2005; Prime version 1.6, Schrödinger, LLC, New York, NY, 2005.
15. S. Patel, L. Vuillard, A. Cleasby, C.W. Murray, and J. Yon J. Mol. Biol. 343 2004 407
16. V. Asso, E. Ghilardi, S. Bertini, M. Digiacomo, C. Granchi, F. Minutolo, S. Rapposelli, A. Bortolato, S. Moro, and M. Macchia ChemMedChem 3 2008 1530
17. H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, and P.E. Bourne Nucleic Acids Res 28 2000 235
18. M.J. Hartshorn, M.L. Verdonk, G. Chessari, S.C. Brewerton, W.T.M. Mooij, P.N. Mortenson, and C.W. Murray J. Med. Chem. 50 2007 726
19. M. Stahl Perspect. Drug Discovery Des. 20 2000 83
20. Glide, version 4.5, Schrödinger, LLC, New York, NY, 2007.
21. MOE (The Molecular Operating Environment) Version 2006.08, software available from Chemical Computing Group Inc., 1010 Sherbrooke Street West, Suite 910, Montreal, Canada H3A 2R7. http://www.chemcomp.com.
22. T. Halgren J. Comput. Chem. 17 1996 490
23. A. Jakalian, D.B. Jack, and C.I. Bayly J. Comput. Chem. 23 2002 1623
24. V. Limongelli, L. Marinelli, S. Cosconati, H.A. Braun, B. Schmidt, and E. Novellino ChemMedChem 2 2007 667