Structure-based optimization of oxadiazole-based GSK-3 inhibitors

European Journal of Medicinal Chemistry

Volumn 61, Issue , 2013, Pages 26-40

  Lo Monte, Fabio ^a   Kramer, Thomas ^a   Gu, Jiamin ^a   Brodrecht, Martin ^a   Pilakowski, Johannes ^a   Fuertes, Ana ^b   Dominguez, Juan Manuel ^b   Plotkin, Batya ^c   Eldar Finkelman, Hagit ^c   Schmidt, Boris ^a  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

^b Drug Discovery   (Spain)

^c TEL AVIV UNIVERSITY   (Israel)

Author keywords

Alzheimer's disease; Glycogen synthase Kinase 3 (GSK 3); Reversible inhibition; Structure activity relationship (SAR); Zebrafish phenotype

Indexed keywords

ACETAMIDE; BENZODIOXANE; GLYCOGEN SYNTHASE KINASE 3 INHIBITOR; GLYCOGEN SYNTHASE KINASE 3ALPHA; GLYCOGEN SYNTHASE KINASE 3BETA; MOLECULAR SCAFFOLD; OXADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BIOASSAY; CONTROLLED STUDY; DRUG EFFICACY; DRUG PENETRATION; DRUG SAFETY; DRUG TOXICITY; EMBRYO; IC 50; NONHUMAN; PROCESS OPTIMIZATION; STRUCTURE ANALYSIS; WILD TYPE; ZEBRA FISH;

ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; GLYCOGEN SYNTHASE KINASE 3; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXADIAZOLES; PROTEIN KINASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; ZEBRAFISH;

EID: 84874943660     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.06.006     Document Type: Article

References (54)

1. F. Lo Monte, T. Kramer, A. Boländer, B. Plotkin, H. Eldar-Finkelman, A. Fuertes, J. Dominguez, and B. Schmidt Synthesis and biological evaluation of glycogen synthase kinase 3 (GSK-3) inhibitors: an fast and atom efficient access to 1-aryl-3-benzylureas Bioorg. Med. Chem. Lett. 21 2011 5610 5615
2. C. Hooper, R. Killick, and S. Lovestone The GSK3 hypothesis of Alzheimer's disease J. Neurochem. 104 2008 1433 1439
3. A. Alzheimer Über eine eigenartige Erkankung der Hirnrinde Allgemeine Zeitschrift Für Psychiatrie Und Psychisch-gerichtliche Medizin (Berlin) 64 1907 146 148
4. A. Alzheimer, R.A. Stelzmann, H.N. Schnitzlein, and F.R. Murtagh An English translation of Alzheimer's 1907 paper, Über eine eigenartige Erkankung der Hirnrinde Clin. Anat. 8 1995 429 431
5. P. Cohen, and M. Goedert GSK3 inhibitors: development and therapeutical potential Nat. Rev. Drug Discov. 3 2004 479 487
6. F. Hernández, and J. Avila The role of glycogen synthase kinase 3 in the early stages of Alzheimers' disease FEBS Lett. 582 2008 3848 3854
7. Eldar-Finkelman Glycogen synthase kinase 3: an emerging therapeutic target Trends Mol. Med. 8 2002 126 132
8. M. Mazanetz, and P. Fischer Untangling tau hyperphosphorylation in drug design for neurodegenerative diseases Nat. Rev. Drug Discov. 6 2007 464 479
9. L. Chico, L. Van Eldik, and D. Watterson Targeting protein kinases in central nervous system disorders 892-909 Nat. Rev. Drug Discov. 8 2009
10. L. Meijer, M. Flajolet, and P. Greengard Pharmacological inhibitors of glycogen synthase kinase 3 TRENDS. Pharmacol. Sci. 25 2004 471 480
11. A. Martinez, C. Gil, and D.I. Perez Glycogen synthase kinase 3 inhibitors in the next horizon for Alzheimer's disease treatment Int. J. of Alzheimer's Disease 2011 2011 1 7
12. K.F. Lau, C.C.J. Miller, B.H. Anderton, and P.C. Shaw Expression analysis of glycogen synthase kinase-3 in human tissues J. Pept. Res. 54 1999 85 91
13. S. Frame, and P. Cohen GSK3 takes centre stage more than 20 years after its discovery Biochem. J. 359 2001 1 16
14. E. Hur, and F. Zhou GSK3 signalling in neural development Nat. Rev. Neurosci. 11 2010 539 551
15. F. Mukai, K. Ishiguro, Y. Sano, and S.C. Fujita Alternative splicing isoform of tau protein kinase I/glycogen synthase kinase 3 beta J. Neurochem. 81 2002 1073 1083
16. E. ter Haar, J.T. Coll, D.A. Austen, H. Hsiao, L. Swenson, and J. Jain Structure of GSK3β reveals a primed phosphorylation mechanism Nat. Struct. Biol. 8 2001 593 596
17. R. Dajani, E. Fraser, S.M. Roe, N. Young, V. Good, T.C. Dale, and L.H. Pearl Crystal structure of glycogen synthase kinase 3: structural basis for phosphate-primed substrate specificity and autoinhibition Cell 105 2001 721 732
18. A. Takashima Drug development targeting the glycogen synthase kinase-3β (GSK-3β)-mediated signal transduction pathway: role of GSK-3β in adult brain J. Pharmacol. Sci. 109 2009 174 178
19. L. Serenó, M. Coma, M. Rodriguez, P. Sánchez-Ferrer, M.B. Sánchez, I. Gich, J.M. Agulló, J. Avila, M. Pérez, C. Guardia-Laguarta, J. Clarimón, A. Lleó, and T. Gómez-Isla A novel GSK-3β inhibitor reduces Alzheimer's pathology and rescues neuronalloss in vivo Neurobiol. Dis. 35 2009 359 367
20. H. Yamaguchi, K. Ishiguro, T. Uchida, A. Takashima, C.A. Lemere, and K. Imahori Preferential labeling of Alzheimer neurofibrillary tangles with antisera for tau protein kinase (TPK) I/glycogen synthase kinase-3β and cyclin-dependent kinase 5, a component of TPK II Acta Neuropathol. 92 1996 232 241
21. A. Martinez, A. Castro, I. Dorronsoro, and M. Alonso Glycogen synthase kinase 3 (GSK-3) inhibitors as new promising drugs for diabetes, neurodegeneration, cancer, and inflammation Med. Res. Rev. 22 2002 373 384
22. L. Feng, Y. Geisselbrecht, S. Blanck, A. Wilbuer, G.E. Atilla-Gokcumen, P. Filippakopoulos, K. Krling, M.A. Celik, K. Harms, J. Maksimoska, R. Marmorstein, G. Frenking, S. Knapp, L. Essen, and E. Meggers Structurally sophisticated octahedral metal complexes as highly selective protein kinase inhibitors J. Am. Chem. Soc. 133 2011 5976 5986
23. R.V. Bhat, S.L. Budd Haeberlein, and J. Avila Glycogen synthase kinase 3: a drug target for CNS therapies J. Neurochem. 89 2004 1313 1317
24. F. Lo Monte, T. Kramer, J. Gu, U. Rao Anumala, L. Marinelli, V. La Pietra, E. Novellino, B. Franco, D. Demedts, F. Van Leuven, A. Fuertes, J.M. Dominguez, B. Plotkin, H. Eldar-Finkelman, and B. Schmidt Identification of glycogen synthase Kinase-3 inhibitors with a selective sting for glycogen synthase Kinase-3α J. Med. Chem. 55 2012 4407 4424
25. T. Kramer, B. Schmidt, and F. Lo Monte Small-molecule inhibitors of GSK-3-Structural insights and their application to Alzheimer's disease models Int. J. of Alzheimer's Disease 2012 accepted http://www.hindawi.com/journals/ ijad/aip/381029/
26. B. Voigt, M. Krug, C. Schächtele, F. Totzke, and A. Hilgeroth Probing novel 1-Aza-9-oxafluorenes as selective GSK-3β inhibitors ChemMedChem 3 2008 120 126
27. J. Boström, A. Hogner, A. Llinás, E. Wellner, and A.T. Plowright Oxadiazoles in medicinal chemistry J. Med. Chem. 55 2012 1817 1830
28. M. Saitoh, J. Kunitomo, E. Kimura, Y. Hayase, H. Kobayashi, N. Uchiyama, T. Kawamoto, T. Tanaka, C.D. Mol, D.R. Dougan, G.S. Textor, G.P. Snell, and F. Itoh Design, synthesis and structure-activity relationships of 1,3,4-oxadiazole derivatives as novel inhibitors of glycogen synthase kinase-3β Bioorg. Med. Chem. 17 2009 2017 2029
29. L. Naerum, L. Norskov-Lauritsen, and P.H. Olesen Scaffold hopping and optimization towards libraries of glycogen synthase kinase-3 inhibitors Bioorg. Med. Chem. Lett. 12 2002 1525 1528
30. R. Bhat, X. Xue, S. Berg, S. Hellberg, M. Ormö, Y. Nilsson, A. Radesäter, E. Jerning, P. Markgren, M. Nylöf, T. Borgegard, A. Giménez-Cassina, F. Hernández, J.J. Lucas, J. Díaz-Nido, and J. Avila Structural insights and biological effects of glycogen synthase kinase 3-specific inhibitor AR-A014418 J. Biol. Chem. 278 2003 45937 45945
31. H.B. Konig, W. Seifken, and H.A. Offe Sulfur-containing derivatives of pyridine carboxylic acids and compounds derived therefrom Chem. Berichte 87 1954 825 834
32. G. Mazzone, F. Bonina, and R. Arrigo-Reina Synthesis and pharmacological activities of some 2-(alkylaminoalkyl)mercapto-5-aryl-(1,3,4-oxadiazoles) Farmaco, Ed. Scient 32 1977 414 429
33. R.A. Tromp, S. van Ameijde, C. Pütz, C. Sundermann, B. Sundermann, J.K. von Frijtag Drabbe Künzel, and P. IJzerman Inhibition of nucleoside transport by new analogues of 4-nitrobenzylthioinosine: replacement of the ribose moiety by substituted benzyl groups J. Med. Chem. 47 2004 5441 5450
34. S. Chao, S. Li, X. Hui, P. Xu, and L. Dong Synthesis and antibacterial activities of 2-phenyl-5-[[2'-cyano(1,1'-biphenylyl)-4-]methyl]mercapto-1,3,4- oxadiazole Xinxiang Yixueyuan Xuebao 23 2006 5 6
35. S. Giri, H. Singh, and L.D.S. Yadav Studies in oxadiazoles. Synthesis of some 2-mercapto-1,3,4-oxadiazoles and related compounds as potential fungicides Agr. Biol. Chem. 40 1976 17 21
36. M.C. da Silva Lourenco, M. de Lima Ferreira, M.V.N. de Souza, M.A. Peralta, T.R.A. Vasconcelos, and M. das Gracas Henriques Synthesis and anti-mycobacterial activity of (E)-N'-(monosubstituted-benzylidene) isonicotinohydrazide derivatives Eur. J. Med. Chem. 43 2008 1344 1347
37. I. Ninomiya, and O. Yamamoto Photochemistry of isonicotinohydrazide and its analogs in alcohol Heterocycles 4 1976 475 481
38. R.R. Shah, R.D. Mehta, and A.R. Parikh Studies on isoniazid derivatives. Preparation and antimicrobial activity of 2-aryl-3-(pyridylcarbomyl)-5- carboxymethyl-4-thiazolidinones J. Ind. Chem. Soc. 62 1985 255 257
39. S.K. Boovanahalli, X. Jin, Y. Jin, J.H. Kim, N.T. Dat, Y. Hong, J.H. Lee, S. Jung, K. Lee, and J.J. Lee Synthesis of (aryloxyacetylamino)-isonicotinic/ nicotinic acid analogues as potent hypoxia-inducible factor (HIF)-1a inhibitors Bioorg. Med. Chem. Lett. 17 2007 6305 6310
40. M.A. Chowdhury, K.R.A. Abdellatif, Y. Dong, M. Rahman, D. Das, M.R. Suresh, and E.E. Knaus Synthesis of 1-(methanesulfonyl- and aminosulfonylphenyl) acetylenes that possess a 2-(N-difluoromethyl-1,2-dihydropyridin-2-one pharmacophore): evaluation as dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity Bioorg. Med. Chem. Lett. 19 2009 584 588
41. Q. Zheng, F. Zhang, K. Cheng, Y. Yang, Y. Chen, Y. Qian, H. Zhang, L. Li, C. Zhou, S. An, Q. Jiao, and H. Zhu Synthesis, biological evaluation and molecular docking studies of amide-coupled benzoic nitrogen mustard derivatives as potential antitumor agents Bioorg. Med. Chem. 18 2010 880 886
42. A. Molinos-Gómez, X. Vidal, M. Maymó, D. Velasco, J. Martorell, and F. López-Calahorra Tautomeric enhancement of the hyperpolarizability in new acridine-benzothiazolylamine based NLO chromophores Tetrahedron 61 2005 9075 9081
43. K. Yamazaki, Y. Kaneko, K. Suwa, S. Ebara, K. Nakazawa, and K. Yasuno Synthesis of potent and selective inhibitors of Candida albicans N-myristoyltransferase based on the benzothiazole structure Bioorg. Med. Chem. 13 2005 2509 2522
44. P. Basabe, A. Diego, S. Delgado, D. Díez, I.S. Marcos, and J.G. Urones Short and efficient synthesis of (+)-subersic acids Tetrahedron 59 2003 9173 9177
45. M. Ebisawa, M. Ueno, Y. Oshimo, and Y. Kondo Synthesis of dictyomedins using phosphazene base catalyzed diaryl ether formation Tetrahedron Lett. 48 2007 8918 8921
46. L. Campeau, M. Parisien, A. Jean, and K. Fagnou Catalytic direct arylation with aryl chlorides, bromides, and iodides: intramoleculas studiel leading tn new intermolecular reactions J. Am. Chem. Soc. 128 2006 581 590
47. H.V. Namboodiri, M. Bukhtiyarova, J. Ramcharan, M. Karpusas, Y. Lee, and E.B. Springman Analysis of Imatinib and Sorafenib binding to p38a compared with c-Abl and b-Raf provides structural insights for understanding the selectivity of inhibitors targeting the DFG-Out form of protein kinases Biochemistry 49 2010 3611 3618
48. J.R. Simard, M. Getlik, C. Grütter, V. Pawar, S. Wulfert, M. Rabiller, and D. Rauh Development of a fluorescent-tagged kinase assay system for the detection and characterization of allosteric kinase inhibitors J. Am. Chem. Soc. 131 2009 13286 13296
49. D. Paquet, R. Bhat, A. Sydow, E. Mandelkow, S. Berg, S. Hellberg, J. Fälting, M. Distel, R.W. Köster, B. Schmid, and C. Haass A zebrafish model of tauopathy allows in vivo imaging of neuronal cell death and drug evaluation J. Clin. Invest. 119 2009 1382 1395
50. G.E. Atilla-Gokcumen, D.S. Williams, H. Bregman, N. Pagano, and E. Meggers Organometallic compounds with biological activity: a very selective and highly potent cellular inhibitor for glycogen synthase kinase 3 ChemBioChem 7 2006 1443 1450
51. C.J. Phiel, C.A. Wilson, V.M.Y. Lee, and P.S. Klein GSK-3 alpha regulates production of Alzheimer's disease amyloid-beta peptides Nature 423 2003 435 439
52. M. Cristina da Silva Lourenco, M. de Lima Ferreira, M. Vinícius Nora de Souza, M. Amado Peralta, T. Rocha Alves Vasconcelos, M.O. das Gracas, and M. Henriques Synthesis and anti-mycobacterial activity of (E)-N′-(monosubstituted-benzylidene)isonicotinohydrazide derivatives Eur. J. Med. Chem. 43 2008 1344 1347
53. Z. Liberman, and H. Eldar-Finkelman Serine 332 phosphorylation of insulin receptor substrate-1 by glycogen synthase kinase-3 attenuates insulin signaling J. Biol. Chem. 280 2005 4422 4428
54. C.B. Kimmel, W.W. Ballard, S.R. Kimmel, B. Ullmann, and T.F. Schilling Stages of embryonic development of the zebrafish, develop Dynamics 203 1995 253 310