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Research Paper

Computer-aided molecular design of pyrazolotriazines targeting glycogen synthase kinase 3

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Pages 87-96 | Received 03 May 2018, Accepted 17 Sep 2018, Published online: 26 Oct 2018

References

  • Tarazi H, Odeh RA, Al-Qawasmeh R, et al. Design, synthesis and SAR analysis of potent BACE1 inhibitors: possible lead drug candidates for Alzheimer’s disease. Eur J Med Chem 2017;125:1213–24.
  • Götz J, Schild A, Hoerndli F, Pennanen L. Amyloid-induced neurofibrillary tangle formation in Alzheimer’s disease: insight from transgenic mouse and tissue-culture models. Int J Dev Neurosci 2004;22:453–65.
  • Cutsuridis V, Moustafa AA. Multiscale models of pharmacological, immunological and neurostimulation treatments in Alzheimer’s disease. Drug Discov Today Dis Model 2016;19:85–91.
  • Martinez A, Gil C, Perez DI. Glycogen synthase kinase 3 inhibitors in the next horizon for Alzheimer’s disease treatment. Int J Alzheimers Dis 2011;2011:1–7.
  • Hooper C, Killick R, Lovestone S. The GSK3 hypothesis of Alzheimer’s disease. J Neurochem 2008;104:1433–9.
  • Beurel E, Grieco SF, Jope RJ. Glycogen synthase kinase-3 (GSK3): regulation, actions and diseases. Pharmacol Ther 2015;148:114–31.
  • Hamann M, Alonso D, Martín-Aparicio E. Glycogen synthase kinase-3 (GSK-3) inhibitory activity and structure-activity relationship (SAR) studies of the manzamine alkaloids. Potential for Alzheimer’s disease. J Nat Prod 2007;70:1397–405.
  • Bidon-chanal A, Fuertes A, Alonso D, et al. Evidence for a new binding mode to GSK-3: allosteric regulation by the marine compound palinurin. Eur J Med Chem 2013;60:479–89.
  • Arnost M, Pierce A, Haar E. T, et al. 3-Aryl-4-(arylhydrazono)-1H-pyrazol-5-ones: highly ligand efficient and potent inhibitors of GSK3beta. Bioorg Med Chem Lett 2010;20:1661–4.
  • Patel DS, Bharatam PV. Selectivity criterion for pyrazolo[3,4-b]pyrid[az]ine derivatives as GSK-3 inhibitors: CoMFA and molecular docking studies. Eur J Med Chem 2008;43:949–57.
  • Witherington J, Bordas V, Garland SL, et al. 5-Aryl-pyrazolo[3,4-b]pyridines: potent inhibitors of glycogen synthase kinase-3 (GSK-3). Bioorg Med Chem Lett 2003;13:1577–80.
  • Witherington J, Bordas V, Gaiba A, et al. 6-Heteroaryl-pyrazolo[3,4-b]pyridines: potent and selective inhibitors of glycogen synthase kinase-3 (GSK-3). Bioorg Med Chem Lett 2003;13:3059–62.
  • Witherington J, Bordas V, Haigh D, et al. 5-Aryl-pyrazolo[3,4-b]pyridazines: potent inhibitors of glycogen synthase kinase-3 (GSK-3). Bioorg Med Chem Lett 2003;13:1581–4.
  • Dessalew N, Patel DS, Bharatam PV. 3D-QSAR and molecular docking studies on pyrazolopyrimidine derivatives as glycogen synthase kinase-3beta inhibitors. J Mol Graph Model 2007;25:885–95.
  • Berg S, Bergh M, Hellberg S, et al. Discovery of novel potent and highly selective glycogen synthase kinase-3β (GSK3β) inhibitors for Alzheimer’s disease: design, synthesis, and characterization of pyrazines. J Med Chem 2012;55:9107–19.
  • Martinez A, Alonso M, Castro A, et al. First non-ATP competitive glycogen synthase kinase 3 β (GSK-3β) inhibitors: thiadiazolidinones (TDZD) as potential drugs for the treatment of Alzheimer’s disease. J Med Chem 2002;45:1292–9.
  • Pérez DI, Pistolozzi M, Palomo V, et al. 5-Imino-1,2-4-thiadiazoles and quinazolines derivatives as glycogen synthase kinase β (GSK-3β) and phosphodiesterase 7 (PDE7) inhibitors: determination of blood-brain barrier penetration and binding to human serum albumin. Eur J Pharm Sci 2012;45:677–84.
  • Prati F, De Simone A, Bisignano P, et al. Multitarget drug discovery for Alzheimer’s disease: triazinones as BACE-1 and GSK-3β inhibitors. Angew Chem Int Ed Engl 2015;54:1578–82.
  • Legraverend M. Recent advances in the synthesis of purine derivatives and their precursors. Tetrahedron 2008;64:8585–603.
  • Lim FPL, Dolzhenko AV. 1,3,5-Triazine-based analogues of purine: From isosteres to privileged scaffolds in medicinal chemistry. Eur J Med Chem 2014;85:371–90.
  • Lin C, Sun C, Liu X, et al. Design, synthesis, and in vitro biological evaluation of novel 6-methyl-7-substituted-7-deaza purine nucleoside analogs as anti-influenza A agents. Antiviral Res 2016;129:13–20.
  • Šála M, Kögler M, Placková P, et al. Purine analogs as phosphatidylinositol 4-kinase IIIβ inhibitors. Bioorg Med Chem Lett 2016;26:2706–12.
  • Stamos JL, Chu MLH, Enos MD, et al. Structural basis of GSK-3 inhibition by N-terminal phosphorylation and by the Wnt receptor LRP6. Elife 2014;2014:1–22.
  • Small-Molecule Drug Discovery Suite 2015-3. Schrödinger. New York (NY): LLC; 2015.
  • Forli S, Olson AJ. A force field with discrete displaceable waters and desolvations entropy for hydrated ligand docking. J Med Chem 2012;55:623–38.
  • Cosconati S, Forli S, Perryman AL, et al. Virtual screening with AutoDock: theory and practice. Expert Opin Drug Discov 2010;5:597–607.
  • Morris GM, Huey R, Lindstrom W, et al. Autodock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem 2009;30:2785–91.
  • Radoux CJ, Olsson TSG, Pitt WR, et al. Identifying Interactions that determine fragment binding at protein hotspots. J Med Chem 2016;59:4314–25.
  • Zegzouti H, Zdanovskaia M, Hsiao K, Goueli SA. ADP-Glo: A Bioluminescent and homogeneous ADP monitoring assay for kinases. Assay Drug Dev Technol. 2009;7(6):560–72.
  • Baki A, Bielik A, Molnár L, et al. A high throughput luminescent assay for glycogen synthase kinase-3beta inhibitors. Assay Drug Dev Technol 2007;5:75–84.
  • Colomer JP, Moyano EL. New application of heterocyclic diazonium salts. Synthesis of pyrazolo[3,4-d][1,2,3]triazin-4-ones and imidazo[4,5-d][1,2,3]triazin-4-ones. Tetrahedron Lett 2011;52:1561–5.
  • Leost M, Schultz C, Link A, et al. Paullones are potent inhibitors of glycogen synthase kinase-3β and cyclin-dependent kinase 5/p25. Eur J Biochem 2000;267:5983–94.
  • Corre LL, Tak-Tak L, Guillard A, et al. Microwave-assisted preparation of 4-amino-3-cyano-5-methoxycarbonyl-N-arylpyrazoles as building blocks for the diversity-oriented synthesis of pyrazole-based polycyclic scaffolds. Org Biomol Chem 2015;13:409–23.
  • Desai ND, Shah RD. Improved protocol for Thorpe reaction: synthesis of 4‐amino‐1‐arylpyrazole using solid–liquid phase‐transfer conditions. Synth Commun 2008;38:316–27.
  • Wu M-H, Hu J-H, Shen D-S, et al. Regiospecific synthesis of 6-aryl-3-cyano-5-alkylamino/arylamino-1-p-tolyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-ones via iminophosphorane-mediated annulation. Tetrahedron 2010;66:5112–20.
  • Kamal A, Sastry KNV, Chandrasekhar D, et al. One-pot, three-component approach to the synthesis of 3,4,5-trisubstituted pyrazoles. J Org Chem 2015;80:4325–35.
  • Ledenyova IV, Didenko VV, Shikhaliev KS. Chemistry of pyrazolo-3(5)-diazonium salts (review). Chem Heterocycl Compd 2014;50:1214–43.
  • Di L, Kerns EH, Fan K, et al. High throughput artificial membrane permeability assay for blood-brain barrier. Eur J Med Chem 2003;38:223–32.
  • Metin-Armağan D, Gezen-Ak D, Dursun E, et al. J Okadaic acid-induced tau hyperphosphorylation and the downregulation of Pin1 expression in primary cortical neurons. Chem Neuroanat 2018;92:41–7.
  • Wu X, Kosaraju J, Tam KY. SLM, a novel carbazole-based fluorophore attenuates okadaic acid-induced tau hyperphosphorylation via down-regulating GSK-3β activity in SH-SY5Y cells. Eur J Pharm Sci 2017;110:101–8.