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Identification and optimization of N3,N6-diaryl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamines as a novel class of ACK1 inhibitors.

Kopecky DJ, Hao X, Chen Y, Fu J, Jiao X, Jaen JC, Cardozo MG, Liu J, Wang Z, Walker NP, Wesche H, Li S, Farrelly E, Xiao SH, Kayser F
Bioorg Med Chem Lett 18 6352-6 (2008)
Cited: 19 times
EuropePMC logo PMID: 18993068

Abstract

A new series of pyrazolo[3,4-d]pyrimidine-3,6-diamines was designed and synthesized as potent and selective inhibitors of the nonreceptor tyrosine kinase, ACK1. These compounds arose from efforts to rigidify an earlier series of N-aryl pyrimidine-5-carboxamides. The synthesis and structure-activity relationships of this new series of inhibitors are reported. The most promising compounds were also profiled for their pharmacokinetic properties.

Articles - 3eqr mentioned but not cited (10)

  1. Methyl effects on protein-ligand binding. Leung CS, Leung SS, Tirado-Rives J, Jorgensen WL. J Med Chem 55 4489-4500 (2012)
  2. Relative Binding Free Energy Calculations Applied to Protein Homology Models. Cappel D, Hall ML, Lenselink EB, Beuming T, Qi J, Bradner J, Sherman W. J Chem Inf Model 56 2388-2400 (2016)
  3. Development of novel ACK1/TNK2 inhibitors using a fragment-based approach. Lawrence HR, Mahajan K, Luo Y, Zhang D, Tindall N, Huseyin M, Gevariya H, Kazi S, Ozcan S, Mahajan NP, Lawrence NJ. J Med Chem 58 2746-2763 (2015)
  4. Ack1: activation and regulation by allostery. Gajiwala KS, Maegley K, Ferre R, He YA, Yu X. PLoS One 8 e53994 (2013)
  5. Estimation of relative free energies of binding using pre-computed ensembles based on the single-step free energy perturbation and the site-identification by Ligand competitive saturation approaches. Raman EP, Lakkaraju SK, Denny RA, MacKerell AD. J Comput Chem 38 1238-1251 (2017)
  6. Identification of gefitinib off-targets using a structure-based systems biology approach; their validation with reverse docking and retrospective data mining. Verma N, Rai AK, Kaushik V, Brünnert D, Chahar KR, Pandey J, Goyal P. Sci Rep 6 33949 (2016)
  7. Survey of phosphorylation near drug binding sites in the Protein Data Bank (PDB) and their effects. Smith KP, Gifford KM, Waitzman JS, Rice SE. Proteins 83 25-36 (2015)
  8. In Silico Investigation of the Anti-Tumor Mechanisms of Epigallocatechin-3-Gallate. Wang W, Xiong X, Li X, Zhang Q, Yang W, Du L. Molecules 24 E1445 (2019)
  9. Efficient Hit-to-Lead Searching of Kinase Inhibitor Chemical Space via Computational Fragment Merging. Andrianov GV, Gabriel Ong WJ, Serebriiskii I, Karanicolas J. J Chem Inf Model 61 5967-5987 (2021)
  10. Identification of Activated Cdc42-Associated Kinase Inhibitors as Potential Anticancer Agents Using Pharmacoinformatic Approaches. Kumar V, Kumar R, Parate S, Danishuddin, Lee G, Kwon M, Jeong SH, Ro HS, Lee KW, Kim SW. Biomolecules 13 217 (2023)


Reviews citing this publication (4)

  1. Profound methyl effects in drug discovery and a call for new C-H methylation reactions. Schönherr H, Cernak T. Angew Chem Int Ed Engl 52 12256-12267 (2013)
  2. ACK1 tyrosine kinase: targeted inhibition to block cancer cell proliferation. Mahajan K, Mahajan NP. Cancer Lett 338 185-192 (2013)
  3. Medicinal attributes of pyrazolo[3,4-d]pyrimidines: a review. Chauhan M, Kumar R. Bioorg Med Chem 21 5657-5668 (2013)
  4. The Deuterated "Magic Methyl" Group: A Guide to Site-Selective Trideuteromethyl Incorporation and Labeling by Using CD3 Reagents. Steverlynck J, Sitdikov R, Rueping M. Chemistry 27 11751-11772 (2021)

Articles citing this publication (5)

  1. High-throughput kinase profiling: a more efficient approach toward the discovery of new kinase inhibitors. Miduturu CV, Deng X, Kwiatkowski N, Yang W, Brault L, Filippakopoulos P, Chung E, Yang Q, Schwaller J, Knapp S, King RW, Lee JD, Herrgard S, Zarrinkar P, Gray NS. Chem Biol 18 868-879 (2011)
  2. A novel multi-modal drug repurposing approach for identification of potent ACK1 inhibitors. Phatak SS, Zhang S. Pac Symp Biocomput 29-40 (2013)
  3. ACK1-AR and AR-HOXB13 signaling axes: epigenetic regulation of lethal prostate cancers. Kim EH, Cao D, Mahajan NP, Andriole GL, Mahajan K. NAR Cancer 2 zcaa018 (2020)
  4. Effect of set up protocols on the accuracy of alchemical free energy calculation over a set of ACK1 inhibitors. Granadino-Roldán JM, Mey ASJS, Pérez González JJ, Bosisio S, Rubio-Martinez J, Michel J. PLoS One 14 e0213217 (2019)
  5. RETRACTED: Design, synthesis, structure-activity relationship and kinase inhibitory activity of substituted 3-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ones. Lamie PF. Bioorg Med Chem Lett 26 3093-3097 (2016)


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