Design, synthesis and biological evaluation of benzothiazepinones (BTZs) as novel non-ATP competitive inhibitors of glycogen synthase kinase-3β (GSK-3β)

European Journal of Medicinal Chemistry

Volumn 61, Issue , 2013, Pages 95-103

  Zhang, Peng ^a   Hu, Hai Rong ^b   Bian, Shi Hui ^a   Huang, Zhao Hui ^a   Chu, Yong ^a   Ye, De Yong ^a  

^a FUDAN UNIVERSITY   (China)

^b FUDAN UNIVERSITY   (China)

Author keywords

Benzothiazepinones; Docking; GSK 3 ; Kinase inhibitor; Non ATP competitive; Selectivity

Indexed keywords

1 TERT BUTYL 3 [6 (3,5 DIMETHOXYPHENYL) 2 (4 DIETHYLAMINOBUTYLAMINO)PYRIDO[2,3 D]PYRIMIDIN 7 YL]UREA; 2,3 DIHYDRO 2 BENZYL 5 (2 NITROBENZYL) 1,5 BENZOTHIAZEPIN 4(5H)ONE; 2,3 DIHYDRO 2 PHENYL 5 (2 NITROBENZYL) 1,5 BENZOTHIAZEPIN 4(5H)ONE; 2,3 DIHYDRO 2 PHENYL 5 (3 CARBOMETHOXYBENZYL) 1,5 BENZOTHIAZEPIN 4(5H)ONE; AFATINIB; BENZOTHIAZEPINONE DERIVATIVE; DASATINIB; GLYCOGEN SYNTHASE KINASE 3 INHIBITOR; GLYCOGEN SYNTHASE KINASE 3BETA; SUNITINIB; UNCLASSIFIED DRUG;

ARTICLE; CELL ASSAY; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG DESIGN; DRUG EFFECT; DRUG SCREENING; DRUG SYNTHESIS; ENZYME BINDING; HUMAN; HYPOTHESIS; IC 50; IN VITRO STUDY; LUMINESCENCE; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION;

BENZAZEPINES; BINDING, COMPETITIVE; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; GLYCOGEN SYNTHASE KINASE 3; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84874936597     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.09.021     Document Type: Article

References (31)

1. P. Cohen, D. Yellowlees, A. Aitken, A. Donella-Deana, B.A. Hemmings, and P.J. Parker Eur. J. Biochem. 124 1982 21 35
2. J.R. Woodgett Sci. STKE 100 2001 12
3. E.M. Hur, and F.Q. Zhou Nat. Rev. Neurosci. 11 2010 539 551
4. A. Kannoji, S. Phukan, V. Sudher Babu, and V.N. Balaji Expert Opin. Ther. Targets 12 2008 1443 1455
5. D. Alonso, and A. Martinez Glycogen Synthase Kinase 3 (GSK-3) and Its Inhibitors 2006 JohnWiley & Sons Hoboken, NJ, USA pp. 307-331
6. A. Martinez, C. Gil, and D.I. Perez Int. J. Alzheimer's Dis. 2011 2011 280502
7. A. Martinez Med. Res. Rev. 28 2008 773 796
8. P. Bamborough, D. Drewry, G. Harper, G.K. Smith, and K. Schneider J. Med. Chem. 51 2008 7898 7914
9. H. Eldar-Finkelman, A. Licht-Murava, S. Pietrokovski, and M. Eisenstein Biochim. Biophys. Acta 1804 2010 598 603
10. A. Martinez, M. Alonso, A. Castro, C. Pérez, and F.J. Moreno J. Med. Chem. 45 2002 1292 1299
11. T. del Ser Alzheimer's Dementia 6 2010 S147
12. S. Conde, D.I. Pérez, A. Martínez, C. Perez, and F.J. Moreno J. Med. Chem. 46 2003 4631 4633
13. D.I. Perez, S. Conde, C. Pérez, C. Gil, D. Simon, F. Wandosell, F.J. Moreno, J.L. Gelpí, F.J. Luque, and A. Martínez Bioorg. Med. Chem. 17 2009 6914 6925
14. D.I. Perez, V. Palomo, C.P. rez, C. Gil, P.D. Dans, F.J. Luque, S. Conde, and A. Martinez J. Med. Chem. 54 2011 4042 4056
15. H. Eldar-Finkelman, and M. Eisenstein Curr. Pharm. Des. 15 2009 2463 2470
16. M. Hamann, D. Alonso, E. Martín-Aparicio, A. Fuertes, M.J. Pérez-Puerto, A. Castro, S. Morales, M.L. Navarro, M. del Monte-Millán, and M. Medina J. Nat. Prod. 70 2007 1397 1405
17. J.C. Lancelot, B. Letois, C. Saturnono, P. De Caprariis, and M. Robba Org. Prep. Proced. Int. 24 1992 204 208
18. A. Levai, and H. Duddeck Pharmazie 38 1983 827 828
19. S.F. Wnuk, S.M. Chowdhury, P.I. Garcia Jr., and M.J. Robins J. Org. Chem. 67 2002 1816 1819
20. A. Baki, A. Bielik, L. Molnar, G. Szendrei, and G.M. Keseru Assay Drug Dev. Technol. 5 2007 75 83
21. GOLD, Version 5.0, The Cambridge Crystallographic Data Centre, http://www.ccdc.cam.ac.uk.
22. V. Palomo, I. Soteras, D.I. Perez, C. Perez, C. Gil, N.E. Campillo, and A. Martinez J. Med. Chem. 54 2011 8461 8470
23. Discovery Studio, Version 3.0, Accelrys Software Inc., http://www.accelrys.com.
24. N. Lensen, S. Mouelhi, and M. Bellassoued Synth. Commun. 31 2001 1007 1011
25. M. Bellassoued, N. Lensen, M. Bakasse, and S. Mouelhi J. Org. Chem. 63 1998 8785 8789
26. J. Krapcho, E.R. Spitzmiller, and C.F. Turk J. Med. Chem. 6 1963 544 546
27. A.N. Nesmeyanov, L.I. Zakharkin, and R. Kh Freidlina Dokl. Akad. Nauk SSSR 111 1956 114 116
28. A. Lebedev, A. Lebedeva, V. Sheludyakov, E. Kovaleva, O. Ustinova, and I. Kozhevnikov Russ. J. Gen. Chem. 75 2005 1113 1124
29. P. Ghorai, A. Kraus, M. Keller, C. Gotte, P. Igel, E. Schneider, D. Schnell, G.n. Bernhardt, S. Dove, M. Zabel, S. Elz, R. Seifert, and A. Buschauer J. Med. Chem. 51 2008 7193 7204
30. Y. Wang, J. Ai, Y. Chen, L. Wang, G. Liu, M. Geng, and A. Zhang J. Med. Chem. 54 2011 2127 2142
31. Sybyl Version 6.9, Triops Inc, St. Louis, MO.