Substituted 2-aminothiazoles are exceptional inhibitors of neuronal degeneration in tau-driven models of Alzheimer's disease

European Journal of Pharmaceutical Sciences

Volumn 43, Issue 5, 2011, Pages 386-392

  Lagoja, Irene ^a   Pannecouque, Christophe ^a   Griffioen, Gerard ^b   Wera, Stefaan ^b   Rojasdelaparra, Veronica Maria ^b   Van Aerschot, Arthur ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^b NV ReMYND   (Belgium)

Author keywords

2 Aminothiazole; Alzheimer's disease; Hantzsch synthesis; Neurofibrillary tangles; Neuronal toxicity; Tauopathies

Indexed keywords

2 AMINOTHIAZOLE DERIVATIVE; N (3,5 DIMETHYLPHENYL) 5 ISOPROPYL 4 PHENYLTHIAZOL 2 AMINE; TAU PROTEIN; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; CELL PROTECTION; DRUG POTENCY; DRUG SCREENING; HUMAN; HUMAN CELL; NERVE DEGENERATION; NEUROTOXICITY; ONE POT SYNTHESIS; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TAUOPATHY;

ALZHEIMER DISEASE; CELL LINE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, BIOLOGICAL; NEURONS; TAU PROTEINS; THIAZOLES;

EID: 79960016629     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2011.05.014     Document Type: Article

References (26)

1. ACD-Chem-Sketch. < http://www.acdlabs.com >.
2. P.S. Aisen Alzheimer's disease therapeutic research: the path forward Alzheimers Res. Ther. 1 2009 2
3. P.S. Aisen, D. Saumier, R. Briand, J. Laurin, F. Gervais, P. Tremblay, and D. Garceau A Phase II study targeting amyloid-beta with 3APS in mild-to-moderate Alzheimer disease Neurology 67 2006 1757 1763 (Pubitemid 44900749)
4. C. Ballatore, V.M. Lee, and J.Q. Trojanowski Tau-mediated neurodegeneration in Alzheimer's disease and related disorders Nat. Rev. Neurosci. 8 2007 663 672 (Pubitemid 47283144)
5. Becker, E.D., 1969. High Resolution NMR, third ed. Theory and Chemical Applications, Academic Press, San Diego.
6. G.E. Boswell, D.L. Musso, J.L. Kelley, F.E. Soroko, and B.R. Cooper Synthesis and anti-tetrabenazine activity of C-3 analogues of dimethyl-2-phenylmorpholines J. Heterocyclic Chem. 33 1996 33 39 (Pubitemid 26128970)
7. L. Buee, T. Bussiere, V. Buee-Scherrer, A. Delacourte, and P.R. Hof Tau protein isoforms, phosphorylation and role in neurodegenerative disorders Brain Res. Brain Res. Rev. 33 2000 95 130
8. M. Citron Beta-secretase inhibition for the treatment of Alzheimer's disease - promise and challenge Trends Pharmacol. Sci. 25 2004 92 97 (Pubitemid 38183395)
9. D.I. Dominguez, B. De Strooper, and W. Annaert Secretases as therapeutic targets for the treatment of Alzheimer's disease Amyloid 8 2001 124 142 (Pubitemid 32522158)
10. Evans, D.P., Gordon, J.J., 1938. The influence of alkyl groups upon reaction velocities in solution. Part II. The base-catalysed prototropy of phenyl alkyl ketones. J. Chem. Soc. 1434.
11. A. Gallardo-Godoy, J. Gever, K.L. Fife, B.M. Silber, S.B. Prusiner, and A.R. Renslo 2-Aminothiazoles as therapeutic leads for prion diseases J. Med. Chem. 54 2011 1010 1021
12. A.W. Garofalo Patents targeting γ-secretase inhibition and modulation for the treatment of Alzheimer's disease: 2004-2008 Expert Opin. Ther. Pat. 18 2008 693 703
13. S. Ghaemmaghami, B.C.H. May, A.R. Renslo, and S.B. Prusiner Discovery of 2-aminothiazoles as potent antiprion compounds J. Virol. 84 2010 3408 3412
14. S. Gilman, M. Koller, R.S. Black, L. Jenkins, S.G. Griffith, N.C. Fox, L. Eisner, L. Kirby, M.B. Rovira, F. Forette, and J.M. Orgogozo Clinical effects of Abeta immunization (AN1792) in patients with AD in an interrupted trial Neurology 64 2005 1553 1562 (Pubitemid 40617691)
15. A. Hantzsch Ueber das sogenannte Cyanaceton Ber. Dtsch. Chem. Ges. 23 1890 1472 1474
16. A. Hantzsch, and H.J. Weber Ueber Verbindungen des Thiazols (Pyridins der Thiophenreihe) Ber. Dtsch. Chem. Ges. 20 1887 3118 3132
17. V.M. Lee, M. Goedert, and J.Q. Trojanowski Neurodegenerative tauopathies Annu. Rev. Neurosci. 24 2001 1121 1159 (Pubitemid 32695256)
18. Neurogenetic Pharmaceuticals, I., 2004. Compounds and Uses Thereof in Modulating Amyloid Beta, USA.
19. I. Neurogenetic Pharmaceuticals Compounds and uses thereof in modulating amyloid beta 2010 Neurogenetic Pharmaceuticals, Inc. USA
20. J.G. Schantl, and I.M. Lagoja Expedient synthesis of N-substituted 2-aminothiazoles Synth. Commun. 28 1998 1451 1462 (Pubitemid 28260954)
21. L. Serneels, J. Van Biervliet, K. Craessaerts, T. Dejaegere, K. Horre, T. Van Houtvin, H. Esselmann, S. Paul, M.K. Schafer, O. Berezovska, B.T. Hyman, B. Sprangers, R. Sciot, L. Moons, M. Jucker, Z. Yang, P.C. May, E. Karran, J. Wiltfang, R. D'Hooge, and B. De Strooper Gamma-secretase heterogeneity in the Aph1 subunit: relevance for Alzheimer's disease Science 324 2009 639 642
22. M. Stevens, J. Balzarini, I.M. Lagoja, B. Noppen, K. Francois, A. Van Aerschot, P. Herdewijn, E. De Clercq, and C. Pannecouque Inhibition of human immunodeficiency virus type 1 transcription by N-aminoimidazole derivatives Virology 365 2007 220 237 (Pubitemid 46907233)
23. Y.H. Suh, and F. Checler Amyloid precursor protein, presenilins, and alpha-synuclein: molecular pathogenesis and pharmacological applications in Alzheimer's disease Pharmacol. Rev. 54 2002 469 525
24. R.J. van Marum Do amyloid-lowering strategies work clinically? Ther. Adv. Neurol. Disord. 2 2009 3 6
25. VCCLAB, 2005. Virtual Computational Chemistry Laboratory. < http://www.vcclab.org >.
26. S. Weggen, J.L. Eriksen, P. Das, S.A. Sagi, R. Wang, C.U. Pietrzik, K.A. Findlay, T.E. Smith, M.P. Murphy, T. Bulter, D.E. Kang, N. Marquez-Sterling, T.E. Golde, and E.H. Koo A subset of NSAIDs lower amyloidogenic Abeta42 independently of cyclooxygenase activity Nature 414 2001 212 216 (Pubitemid 33051236)