Comparative molecular field analysis and comparative molecular similarity indices analysis of hydroxyethylamine derivatives as selective human BACE-1 inhibitor

Molecular Diversity

Volumn 14, Issue 1, 2010, Pages 39-49

  Pandey, Ashish ^a   Mungalpara, Jignesh ^a   Mohan, C Gopi ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

3D QSAR; Alzheimer's disease; BACE; CoMFA; CoMSIA

Indexed keywords

BETA SECRETASE; BETA SITE AMYLOID PRECURSOR PROTEIN CLEAVAGE ENZYME 1; ENZYME INHIBITOR; HYDROXYETHYLAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG DESIGN; MOLECULAR MODEL; PHARMACOPHORE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; THREE DIMENSIONAL IMAGING;

ALZHEIMER DISEASE; AMYLOID PRECURSOR PROTEIN SECRETASES; ASPARTIC ACID ENDOPEPTIDASES; DRUG DESIGN; ETHANOLAMINES; HUMANS; LEAST-SQUARES ANALYSIS; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77149154078     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-009-9139-7     Document Type: Article

References (30)

1. SL Cole R Vassar 2008 BACE1 structure and function in health and Alzheimer's disease Curr Alzheimer Res 5 2 100 120 10.2174/156720508783954758 10.2174/156720508783954758 1:CAS:528:DC%2BD1cXkt1als70%3D 18393796
2. T Guo DW Hobbs 2006 Development of BACE1 inhibitors for Alzheimer's disease Curr Med Chem 13 1811 1829 10.2174/092986706777452489 10.2174/092986706777452489 1:CAS:528:DC%2BD28XmtVaisLs%3D 16787223 (Pubitemid 43871758)
3. R Vassar BD Bennett S Babu-Khan S Kahn EA Mendiaz P Denis DB Teplow S Ross P Amarante R Loeloff Y Luo S Fisher J Fuller S Edenson J Lile MA Jarosinski AL Biere E Curran T Burgess J-C Louis F Collins J Treanor G Rogers M Citron 1999 Beta-secretase cleavage of Alzheimer's amyloid precursor protein by the transmembrane aspartic protease BACE Science 286 735 741 10.1126/science.286. 5440.735 10.1126/science.286.5440.735 1:CAS:528:DyaK1MXntFWit74%3D 10531052 (Pubitemid 29505878)
4. C Dingwall 2001 Spotlight on BACE: the secretases as targets for treatment in Alzheimer disease J Clin Invest 108 1243 1246 1:CAS:528: DC%2BD3MXot12ksb4%3D 11696563
5. H Cai Y Wang D McCarthy H Wen DR Borchelt DL Price PC Wong 2001 BACE1 is the major bold beta-secretase for generation of A bold beta peptides by neurons Nat Neurosci 4 233 234 10.1038/85064 10.1038/85064 1:CAS:528: DC%2BD3MXhsF2rtbc%3D 11224536 (Pubitemid 32194867)
6. JN Freskos YM Fobian TE Benson MJ Bienkowski DL Brown TL Emmons R Heintz A Laborde JJ McDonald BV Mischke JM Molyneaux JB Moon PB Mullins PD Bryan DJ Paddock AG Tomasselli G Winterrowd 2007 Design of potent inhibitors of human β-secretase Part 1 Bioorg Med Chem Lett 17 73 77 10.1016/j.bmcl.2006.09.092 (Pubitemid 44959985)
7. JN Freskos YM Fobian TE Benson JB Moon MJ Bienkowski DL Brown TL Emmons R Heintz A Laborde JJ McDonald BV Mischke JM Molyneaux PB Mullins PD Bryan DJ Paddock AG Tomasselli G Winterrowd 2007 Design of potent inhibitors of human β-secretase Part 2 Bioorg Med Chem Lett 17 78 81 10.1016/j.bmcl.2006.09.091 (Pubitemid 44959984)
8. B Clarke E Demont C Dingwall R Dunsdon A Faller J Hawkins I Hussain D MacPherson G Maile R Matico P Milner J Mosley A Naylor A O'Brien S Redshaw D Riddell P Rowland V Soleil KJ Smith S Stanway G Stemp S Sweitzer P Theobald D Vesey DS Walter J Ward G Wayne 2008 BACE-1 inhibitors Part 1: identification of novel hydroxy ethylamines (HEAs) Bioorg Med Chem Lett 18 1011 1016 10.1016/j.bmcl.2007.12.017 10.1016/j.bmcl.2007.12.017 1:CAS:528: DC%2BD1cXhsFWlsLw%3D 18171614 (Pubitemid 351179341)
9. B Clarke E Demont C Dingwall R Dunsdon A Faller J Hawkins I Hussain D MacPherson G Maile R Matico P Milner J Mosley A Naylor A O'Brien S Redshaw D Riddell P Rowland V Soleil KJ Smith S Stanway G Stemp S Sweitzer P Theobald D Vesey DS Walter J Ward G Wayne 2008 BACE-1 inhibitors Part-2: identification of hydroxyl ethylamines (HEAs) with reduced peptidic character Bioorg Med Chem Lett 18 1017 1021 10.1016/j.bmcl.2007.12.019 10.1016/j.bmcl.2007.12.019 1:CAS:528:DC%2BD1cXhsFWlsLs%3D 18166458 (Pubitemid 351179342)
10. P Beswick N Charrier, et al. 2008 BACE-1 inhibitors part 3: identification of hydroxyl ethylamines (HEAs) with nanomolar potency in cells Bioorg Med Chem Lett 18 1022 1026 10.1016/j.bmcl.2007.12.020 10.1016/j.bmcl.2007.12.020 1:CAS:528:DC%2BD1cXhsFWlsLc%3D 18171615 (Pubitemid 351179343)
11. H Park K Min HS Kwak KD Koo D Lim SW Seo JU Choi B Platt DY Choi 2008 Synthesis, SAR, and X-ray structure of human BACE-1 inhibitors with cyclic urea derivatives Bioorg Med Chem Lett 18 2900 2904 10.1016/j.bmcl.2008.03.081 10.1016/j.bmcl.2008.03.081 1:CAS:528:DC%2BD1cXlvVWjsLo%3D 18434152 (Pubitemid 351622045)
12. U Iserloh Y Wu JN Cumming J Pan LY Wang AW Stamford ME Kennedy R Kuvelkar X Chen EM Parker C Strickland J Voigt 2008 Potent pyrrolidine- and piperidine-based BACE-1 inhibitors Bioorg Med Chem Lett 18 414 417 10.1016/j.bmcl.2007.10.116 10.1016/j.bmcl.2007.10.116 1:CAS:528: DC%2BD1cXis1Wgtg%3D%3D 18023580
13. JN Cumming TX Le S Babu C Carroll X Chen L Favreau P Gaspari T Guo DW Hobbs Y Huang U Iserloh ME Kennedy R Kuvelkar G Li J Lowrie NA McHugh L Ozgur J Pan EM Parker K Saionz AW Stamford C Strickland D Tadesse J Voigt L Wang Y Wu L Zhang Q Zhang 2008 Rational design of novel, potent piperazinone and imidazolidinone BACE1 inhibitors Bioorg Med Chem Lett 18 3236 3241 10.1016/j.bmcl.2008.04.050 10.1016/j.bmcl.2008.04.050 1:CAS:528: DC%2BD1cXms1yiu7k%3D 18468890 (Pubitemid 351718333)
14. MK Holloway GB McGaughey CA Coburn SJ Stachel KG Jones EL Stanton AR Gregro MT Lai MC Crouthamel BL Pietrak SK Munshi 2007 Evaluating scoring functions for docking and designing β-secretase inhibitors Bioorg Med Chem Lett 17 823 827 10.1016/j.bmcl.2006.11.090 10.1016/j.bmcl.2006.10.051 1:CAS:528:DC%2BD2sXotFaluw%3D%3D (Pubitemid 46251483)
15. RS Lindsley KP Moore HA Rajapakse HG Selnick MB Young H Zhu S Munshi L Kuo GB McGaughey D Colussi MC Crouthamel MT Lai B Pietrak EA Price S Sankaranarayanan AJ Simon GR Seabrook DJ Hazuda NT Pudvah JH Hochman SL Graham JP Vaccaa PG Nantermeta 2007 Design, synthesis, and SAR of macrocyclic tertiary carbinamine BACE-1 inhibitors Bioorg Med Chem Lett 17 4057 4061 10.1016/j.bmcl.2007.04.072 10.1016/j.bmcl.2007.04.072 1:CAS:528: DC%2BD2sXmvVCks7o%3D 17482814 (Pubitemid 46920916)
16. SJ Stachel CA Coburn TG Steele MC Crouthamel BL Pietrak MT Lai MK Holloway SK Munshi SL Graham JP Vacca 2006 Conformationally biased P3 amide replacements of β-secretase inhibitors Bioorg Med Chem Lett 16 641 644 10.1016/j.bmcl.2005.10.032 10.1016/j.bmcl.2005.10.032 1:CAS:528: DC%2BD2MXhtlCiu7nL 16263281 (Pubitemid 43014850)
17. S Geschwindner LL Olsson JS Albert J Deinum PD Edwards TD Beer RHA Folmer 2007 Discovery of a novel warhead against β-secretase through fragment-based lead generation J Med Chem 50 5903 5911 10.1021/jm070825k 10.1021/jm070825k 1:CAS:528:DC%2BD2sXht1KitrrJ 17985861
18. LD Jennings DC Cole JR Stock MN Sukhdeo JW Ellingboe R Cowling G Jin ES Manas KY Fan MS Malamas BL Harrison S Jacobsen R Chopra PA Lohse WJ Moore MM O'Donnell Y Hu AJ Robichaud MJ Turner E Wagnerf J Bard 2008 Acylguanidine inhibitors of β-secretase: optimization of the pyrrole ring substituents extending into the $${{S}-{1}{\prime}}$$ substrate binding pocket Bioorg Med Chem Lett 18 767 771 10.1016/j.bmcl.2007.11.043 10.1016/j.bmcl.2007.11.043 1:CAS:528:DC%2BD1cXosFWrsQ%3D%3D 18068983
19. D Huang U Lüthi P Kolb M Cecchini A Barberis A Caflisch 2006 In silico discovery of β-secretase inhibitors J Am Chem Soc 128 5436 5443 10.1021/ja0573108 10.1021/ja0573108 1:CAS:528:DC%2BD28XivFWlsro%3D 16620115
20. H Kubinyi 2006 Changing paradigms in drug discovery Spec Publ R Soc Chem 304 219
21. M Awale CG Mohan 2008 Molecular docking guided 3D-QSAR CoMFA analysis of N-4-Pyrimidinyl-1H-indazol-4-amine inhibitors of leukocyte-specific protein tyrosine kinase J Mol Model 14 937 947 10.1007/s00894-008-0334-8 10.1007/s00894-008-0334-8 1:CAS:528:DC%2BD1MXhtFaqs7s%3D 18626671
22. M Awale CG Mohan 2008 3D QSAR CoMFA analysis of C5 substituted pyrrolotriazines as HER2 (ErbB2) inhibitors J Mol Graph Model 26 1169 1178 10.1016/j.jmgm.2007.10.008 10.1016/j.jmgm.2007.10.008 1:CAS:528: DC%2BD1cXjtlyjtbk%3D 18055238
23. D Garg T Gandhi CG Mohan 2008 Exploring QSTR and toxicophore of hERG K+ channel blockers using GFA and HypoGen techniques J Mol Graph Model 26 966 976 10.1016/j.jmgm.2007.08.002 10.1016/j.jmgm.2007.08.002 1:CAS:528: DC%2BD2sXhsVOksL%2FP 17928249 (Pubitemid 350298017)
24. VN Viswanadhan Y Sun MH Norman 2007 Three-dimensional quantitative structure-activity relationships and activity predictions of human TRPV1 channel antagonists: comparative molecular field analysis and comparative molecular similarity index analysis of cinnamides J Med Chem 50 5608 5619 10.1021/jm070261k 10.1021/jm070261k 1:CAS:528:DC%2BD2sXhtFyhu7rK 17948977 (Pubitemid 350110297)
25. Wold S, Johansson A, Cocchi M (1993) PLS-partial least square projection to latent structures. In: Kubinyi H(eds) 3D-QSAR in drug design: theory, methods and applications. ESCOM, Leiden, pp 523-550
26. RD Cramer III DE Patterson JS Bunce 1988 Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins J Am Chem Soc 110 5959 5967 10.1021/ja00226a005 10.1021/ja00226a005 1:CAS:528:DyaL1cXltVCqsbs%3D (Pubitemid 18213690)
27. SYBYL7.1 Tripos Inc., St. Louis, MO 63144, USA
28. M Clark RD Cramer VN Opdenbosch 1989 Validation of the general purpose Tripos 5.2 force field J Comput Chem 10 982 1012 10.1002/jcc.540100804 10.1002/jcc.540100804 1:CAS:528:DyaK3cXhtlygsbk%3D
29. RD Cramer JD Bunce DE Patterson 1988 Cross-validation, bootstrapping, and partial least squares compared with multiple regression in conventional QSAR studies Quant Struct-Act Relat 7 18 25 10.1002/qsar.19880070105 10.1002/qsar.19880070105
30. N Ostermann J Eder U Eidhoff F Zink U Hassiepen S Worpenberg J Maibaum O Simic U Hommel B Gerhartz 2006 Crystal structure of human BACE2 in complex with a hydroxyethylamine transition-state inhibitor J Mol Biol 355 249 261 10.1016/j.jmb.2005.10.027 10.1016/j.jmb.2005.10.027 1:CAS:528:DC%2BD2MXhtlSjt7bO 16305800 (Pubitemid 41774129)