Ligand-based and e-pharmacophore modeling, 3D-QSAR and hierarchical virtual screening to identify dual inhibitors of spleen tyrosine kinase (Syk) and janus kinase 3 (JAK3)

References

• Adams, C., Aldous, D. J., Amendola, S., Bamborough, P., Bright, C., Crowe, S., … Wyman, B. (2003). Mapping the kinase domain of janus kinase 3. Bioorganic and Medicinal Chemistry Letters, 13, 3105–3110.10.1016/S0960-894X(03)00657-7
   PubMed Web of Science ®Google Scholar
• Akiyama, T., Ishida, J., Nakagawa, S., Ogawara, H., Watanabe, S., Itoh, N., … Fukami, Y. (1987). Genistein, a specific inhibitor of tyrosine-specific protein kinases. Journal of Biolology and Chemistry, 262, 5592–5595.
   PubMed Web of Science ®Google Scholar
• Atwell, S., Adams, J. M., Badger, J., Buchanan, M. D., Feil, I. K., Gao, X., … Buchanan, S. G. (2004). A novel mode of gleevec binding is revealed by the structure of spleen tyrosine kinase. Journal of Biological Chemistry, 279, 55827–55832.10.1074/jbc.M409792200
   PubMed Web of Science ®Google Scholar
• Bender, A., & Glen, R. C. (2005). A discussion of measures of enrichment in virtual screening: Compairing the information content of descriptors with increasing levels of sophistication. Journal of Chemical Information and Modeling, 45, 1369–1375.10.1021/ci0500177
   PubMed Web of Science ®Google Scholar
• Boggon, T. J., Li, Y., Manley, P. W., & Eck, M. J. (2005). Crystal structure of the Jak3 kinase domain in complex with a staurosporine analog. Blood, 106, 996–1002.10.1182/blood-2005-02-0707
   PubMed Web of Science ®Google Scholar
• Brasca, M. G., Nesi, M., Avanzi, N., Ballinari, D., Bandiera, T., Bertrand, J., … Ceriani, L. (2014). Pyrrole-3-carboxamides as potent and selective JAK2 inhibitors. Bioorganic & Medicinal Chemistry, 22, 4998–5012.10.1016/j.bmc.2014.06.025
   PubMed Web of Science ®Google Scholar
• Bratt, O., Häggman, M., Ahlgren, G., Nordle, Ö, Björk, A., & Damber, J. E. (2009). Open-label, clinical phase I studies of tasquinimod in patients with castration-resistant prostate cancer. British Journal of Cancer, 101, 1233–1240.10.1038/sj.bjc.6605322
   PubMed Web of Science ®Google Scholar
• Brown, G. R., Bamford, A. M., Bowyer, J., James, D. S., Rankine, N., Tang, E., … Culbert, E. J. (2000). Naphthyl ketones: a new class of Janus kinase 3 inhibitors. Bioorganic & Medicinal Chemistry Letters, 10, 575–579.10.1016/S0960-894X(00)00051-2
   PubMed Web of Science ®Google Scholar
• Burns, C. J., Bourke, D. G., Andrau, L., Bu, X., Charman, S. A., Donohue, A. C., … Kling, M. R. (2009). Phenylaminopyrimidines as inhibitors of Janus kinases (JAKs). Bioorganic & Medicinal Chemistry Letters, 19, 5887–5892.10.1016/j.bmcl.2009.08.071
   PubMed Web of Science ®Google Scholar
• Castillo, M., Forns, P., Erra, M., Mir, M., López, M., Maldonado, M., … Vidal, B. (2012). Highly potent aminopyridines as Syk kinase inhibitors. Bioorganic & Medicinal Chemistry Letters, 22, 5419–5423.10.1016/j.bmcl.2012.07.045
   PubMed Web of Science ®Google Scholar
• Chen, J. J., Thakur, K. D., Clark, M. P., Laughlin, S. K., George, K. M., Bookland, R. G., … George Zhang, Y. (2006). Development of pyrimidine-based inhibitors of Janus tyrosine kinase 3. Bioorganic and Medicinal Chemistry Letters, 16, 5633–5638.10.1016/j.bmcl.2006.08.022
   PubMed Web of Science ®Google Scholar
• Chrencik, J. E., Patny, A., Leung, I. K., Korniski, B., Emmons, T. L., Hall, T., … Benson, T. E. (2010). Structural and thermodynamic characterization of the TYK2 and JAK3 kinase domains in complex with CP-690550 and CMP-6. Journal of Molecular Biology, 400, 413–433.10.1016/j.jmb.2010.05.020
   PubMed Web of Science ®Google Scholar
• Clark, M. P., George, K. M., Bookland, R. G., Chen, J., Laughlin, S. K., Thakur, K. D., … VanRens, J. C. (2007). Development of new pyrrolopyrimidine-based inhibitors of Janus kinase 3 (JAK3). Bioorganic & Medicinal Chemistry Letters, 17, 1250–1253.10.1016/j.bmcl.2006.12.018
   PubMed Web of Science ®Google Scholar
• Cole, A. G., Bohnstedt, A. C., Paradkar, V., Kingsbury, C., Quintero, J. G., Park, H., … Letourneau, J. J. (2009). 2-Benzimidazolyl-9-(chroman-4-yl)-purinone derivatives as JAK3 inhibitors. Bioorganic & Medicinal Chemistry Letters, 19, 6788–6792.10.1016/j.bmcl.2009.09.080
   PubMed Web of Science ®Google Scholar
• Cramer, R. D., Bunce, J. D., Patterson, D. E., & Frank, I. E. (1988). Crossvalidation, bootstrapping, and partial least squares compared with multiple regression in conventional QSAR studies. Quantitative Structure-Activity Relationships, 7, 18–25.10.1002/qsar.v7:1
   Google Scholar
• Currie, K. S., Kropf, J. E., Lee, T., Blomgren, P., Xu, J., Zhao, Z., … Mitchell, S. A. (2014). Discovery of GS-9973, a selective and orally efficacious inhibitor of spleen tyrosine kinase. Journal of Medicinal Chemistry, 57, 3856–3873.10.1021/jm500228a
   PubMed Web of Science ®Google Scholar
• Cywin, C. L., Zhao, B. P., McNeil, D. W., Hrapchak, M., Prokopowicz, A. S., Goldberg, D. R., … Magolda, R. L. (2003). Discovery and SAR of novel [1, 6] naphthyridines as potent inhibitors of spleen tyrosine kinase (SYK). Bioorganic & Medicinal Chemistry Letters, 13, 1415–1418.10.1016/S0960-894X(03)00163-X
   PubMed Web of Science ®Google Scholar
• de Vicente, J., Lemoine, R., Bartlett, M., Hermann, J. C., Hekmat-Nejad, M., Henningsen, R., … Menke, J. (2014). Scaffold hopping towards potent and selective JAK3 inhibitors: Discovery of novel C-5 substituted pyrrolopyrazines. Bioorganic & Medicinal Chemistry Letters, 24, 4969–4975.10.1016/j.bmcl.2014.09.031
   PubMed Web of Science ®Google Scholar
• Dearden, J. C. (2016). The history and development of quantitative structure-activity relationships (QSARs). International Journal of Quantitative Structure-Property Relationships, 1, 1–44.10.4018/IJQSPR
   Google Scholar
• Dixon, S. L., Smondyrev, A. M., Knoll, E. H., Rao, S. N., Shaw, D. E., & Friesner, R. A. (2006). PHASE: A new engine for pharmacophore perception, 3D QSAR model development, and 3D database screening: 1. Methodology and preliminary results. Journal of Computer Aided Molecular Design, 20, 647–671.10.1007/s10822-006-9087-6
   PubMed Web of Science ®Google Scholar
• Duan, J. J. W., Lu, Z., Jiang, B., Yang, B. V., Doweyko, L. M., Nirschl, D. S., … Tokarski, J. S. (2014). Discovery of pyrrolo [1, 2-b] pyridazine-3-carboxamides as Janus kinase (JAK) inhibitors. Bioorganic & Medicinal Chemistry Letters, 24, 5721–5726.10.1016/j.bmcl.2014.10.061
   PubMed Web of Science ®Google Scholar
• Forns, P., Esteve, C., Taboada, L., Alonso, J. A., Orellana, A., Maldonado, M., … Vidal, B. (2012). Pyrazine-based Syk kinase inhibitors. Bioorganic & Medicinal Chemistry Letters, 22, 2784–2788.10.1016/j.bmcl.2012.02.087
   PubMed Web of Science ®Google Scholar
• Forsyth, T., Kearney, P. C., Kim, B. G., Johnson, H. W., Aay, N., Arcalas, A., … Epshteyn, S. (2012). SAR and in vivo evaluation of 4-aryl-2-aminoalkylpyrimidines as potent and selective Janus kinase 2 (JAK2) inhibitors. Bioorganic & Medicinal Chemistry Letters, 22, 7653–7658.10.1016/j.bmcl.2012.10.007
   PubMed Web of Science ®Google Scholar
• Friesner, R. A., Banks, J. L., Murphy, R. B., Halgren, T. A., Klicic, J. J., Mainz, D. T., … Shenkin, P. S. (2004). Glide: A new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. Journal of Medicinal Chemistry, 47, 1739–1749.10.1021/jm0306430
   PubMed Web of Science ®Google Scholar
• Gerspacher, M., Furet, P., Pissot-Soldermann, C., Gaul, C., Holzer, P., Vangrevelinghe, E., … Drueckes, P. (2010). 2-Amino-aryl-7-aryl-benzoxazoles as potent, selective and orally available JAK2 inhibitors. Bioorganic and Medicinal Chemistry Letters, 20, 1724–1727.10.1016/j.bmcl.2010.01.069
   PubMed Web of Science ®Google Scholar
• Giordano, S., & Petrelli, A. (2008). From single-to multi-target drugs in cancer therapy: when a specificity becomes an advantage. Current Medicinal Chemistry, 15, 422–432.10.2174/092986708783503212
   PubMed Web of Science ®Google Scholar
• Glide. (2012). Version 5.8, User manual. New York, NY: Schrödinger, LLC.
   Google Scholar
• Golbraikh, A., & Tropsha, A. (2002). Beware of q2! Journal of Molecular Graphics and Modelling, 20, 269–276.10.1016/S1093-3263(01)00123-1
   PubMed Web of Science ®Google Scholar
• Gossage, L., & Eisen, T. (2010). Targeting multiple kinase pathways: A change in paradigm. Clinical Cancer Research, 16, 1973–1978.10.1158/1078-0432.CCR-09-3182
   PubMed Web of Science ®Google Scholar
• Harikrishnan, L. S., Kamau, M. G., Wan, H., Inghrim, J. A., Zimmermann, K., Sang, X., … Poss, M. A. (2011). Pyrrolo [1, 2-f] triazines as JAK2 inhibitors: achieving potency and selectivity for JAK2 over JAK3. Bioorganic & Medicinal Chemistry Letters, 21, 1425–1428.10.1016/j.bmcl.2011.01.022
   PubMed Web of Science ®Google Scholar
• Hirabayashi, A., Mukaiyama, H., Kobayashi, H., Shiohara, H., Nakayama, S., Ozawa, M., … Isaji, M. (2008a). Structure – activity relationship studies of imidazo [1, 2-c] pyrimidine derivatives as potent and orally effective Syk family kinases inhibitors. Bioorganic & Medicinal Chemistry, 16, 9247–9260.10.1016/j.bmc.2008.09.015
   PubMed Web of Science ®Google Scholar
• Hirabayashi, A., Mukaiyama, H., Kobayashi, H., Shiohara, H., Nakayama, S., Ozawa, M., … Isaji, M. (2008b). A novel Syk family kinase inhibitor: Design, synthesis, and structure–activity relationship of 1, 2, 4-triazolo [4, 3-c] pyrimidine and 1, 2, 4-triazolo [1, 5-c] pyrimidine derivatives. Bioorganic & Medicinal Chemistry, 16, 7347–7357.10.1016/j.bmc.2008.06.017
   PubMed Web of Science ®Google Scholar
• Hisamichi, H., Naito, R., Toyoshima, A., Kawano, N., Ichikawa, A., Orita, A., … Tsukamoto, S. (2005). Synthetic studies on novel Syk inhibitors. Part 1: Synthesis and structure-activity relationships of pyrimidine-5-carboxamide derivatives. Bioorganic & Medicinal Chemistry, 13, 4936–4951.10.1016/j.bmc.2005.05.033
   PubMed Web of Science ®Google Scholar
• Ioannidis, S., Lamb, M. L., Davies, A. M., Almeida, L., Su, M., Bebernitz, G., … Zinda, M. (2009). Discovery of pyrazol-3-ylamino pyrazines as novel JAK2 inhibitors. Bioorganic & Medicinal Chemistry Letters, 19, 6524–6528.10.1016/j.bmcl.2009.10.054
   PubMed Web of Science ®Google Scholar
• Jaime-Figueroa, S., De Vicente, J., Hermann, J., Jahangir, A., Jin, S., Kuglstatter, A., … Shao, A. (2013). Discovery of a series of novel 5H-pyrrolo [2, 3-b] pyrazine-2-phenyl ethers, as potent JAK3 kinase inhibitors. Bioorganic & Medicinal Chemistry Letters, 23, 2522–2526.10.1016/j.bmcl.2013.03.015
   PubMed Web of Science ®Google Scholar
• Jasuja, H., Chadha, N., Kaur, M., & Silakari, O. (2014). Dual inhibitors of Janus kinase 2 and 3 (JAK2/3): Designing by pharmacophore-and docking-based virtual screening approach. Molecular Diversity, 18, 253–267.10.1007/s11030-013-9497-z
   PubMed Web of Science ®Google Scholar
• Kaur, M., Kumari, A., Bahia, M. S., & Silakari, O. (2013). Designing of new multi-targeted inhibitors of spleen tyrosine kinase (Syk) and zeta-associated protein of 70 kDa (ZAP-70) using hierarchical virtual screening protocol. Journal of Molecular Graphics and Modelling, 39, 165–175.10.1016/j.jmgm.2012.11.011
   PubMed Web of Science ®Google Scholar
• Knapp, S., & Sundström, M. (2014). Recently targeted kinases and their inhibitors – The path to clinical trials. Current Opinion in Pharmacology, 17, 58–63.10.1016/j.coph.2014.07.015
   PubMed Web of Science ®Google Scholar
• Kozlov, G., Vinaik, R., & Gehring, K. (2013). Triosephosphate isomerase is a common crystallization contaminant of soluble His-tagged proteins produced in Escherichia coli. Acta Crystallographica Section F: Structural Biology Communications, 69, 499–502.
   Web of Science ®Google Scholar
• Kuethe, J. T., Wong, A., Qu, C., Smitrovich, J., Davies, I. W., & Hughes, D. L. (2005). Synthesis of 5-Substituted-1H-indol-2-yl-1H-quinolin-2-ones: A novel class of KDR kinase inhibitors. The Journal of Organic Chemistry, 70, 2555–2567.10.1021/jo0480545
   PubMed Web of Science ®Google Scholar
• Kumar, B. V., Kotla, R., Buddiga, R., Roy, J., Singh, S. S., Gundla, R., … Sarma, J. A. (2011). Ligand-based and structure-based approaches in identifying ideal pharmacophore against c-Jun N-terminal kinase-3. Journal of Molecular Modeling, 17, 151–163.10.1007/s00894-010-0701-0
   PubMed Web of Science ®Google Scholar
• Kyttaris, V. (2012). Kinase inhibitors: A new class of antirheumatic drugs. Drug Design, Development and Therapy, 6, 245–250.10.2147/DDDT
   PubMed Web of Science ®Google Scholar
• Lai, J. Y., Cox, P. J., Patel, R., Sadiq, S., Aldous, D. J., Thurairatnam, S., … Fenton, G. (2003). Potent small molecule inhibitors of spleen tyrosine kinase (Syk). Bioorganic & Medicinal Chemistry Letters, 13, 3111–3114.10.1016/S0960-894X(03)00658-9
   PubMed Web of Science ®Google Scholar
• Liddle, J., Atkinson, F. L., Barker, M. D., Carter, P. S., Curtis, N. R., Davis, R. P., … Gray, M. (2011). Discovery of GSK143, a highly potent, selective and orally efficacious spleen tyrosine kinase inhibitor. Bioorganic & Medicinal Chemistry Letters, 21, 6188–6194.
   PubMed Web of Science ®Google Scholar
• Ligprep. (2012). Version 2.5, user manual, New Yorkm, NY: Schrödinger, LLC.
   Google Scholar
• Lu, S. H., Wu, J. W., Liu, H. L., Zhao, J. H., Liu, K. T., Chuang, C. K., … Ho, Y. (2011). The discovery of potential acetylcholinesterase inhibitors: A combination of pharmacophore modeling, virtual screening, and molecular docking studies. Journal of Biomedical Sciences, 18, 1–13.
   PubMed Web of Science ®Google Scholar
• Lucas, M. C., Goldstein, D. M., Hermann, J. C., Kuglstatter, A., Liu, W., Luk, K. C., … Liao, C. (2012). Rational design of highly selective spleen tyrosine kinase inhibitors. Journal of Medicinal Chemistry, 55, 10414–10423.10.1021/jm301367c
   PubMed Web of Science ®Google Scholar
• Lynch, S. M., DeVicente, J., Hermann, J. C., Jaime-Figueroa, S., Jin, S., Kuglstatter, A., … Patel, V. (2013). Strategic use of conformational bias and structure based design to identify potent JAK3 inhibitors with improved selectivity against the JAK family and the kinome. Bioorganic & Medicinal Chemistry Letters, 23, 2793–2800.10.1016/j.bmcl.2013.02.012
   PubMed Web of Science ®Google Scholar
• Malerich, J. P., Lam, J. S., Hart, B., Fine, R. M., Klebansky, B., Tanga, M. J., & D’Andrea, A. (2010). Diamino-1, 2, 4-triazole derivatives are selective inhibitors of TYK2 and JAK1 over JAK2 and JAK3. Bioorganic & Medicinal Chemistry Letters, 20, 7454–7457.10.1016/j.bmcl.2010.10.026
   PubMed Web of Science ®Google Scholar
• McDonnell, M. E., Bian, H., Wrobel, J., Smith, G. R., Liang, S., Ma, H., & Reitz, A. B. (2014). Anilino-monoindolylmaleimides as potent and selective JAK3 inhibitors. Bioorganic & Medicinal Chemistry Letters, 24, 1116–1121.10.1016/j.bmcl.2014.01.001
   PubMed Web of Science ®Google Scholar
• McLean, L. R., Zhang, Y., Zaidi, N., Bi, X., Wang, R., Dharanipragada, R., … Kominos, D. (2012). X-ray crystallographic structure-based design of selective thienopyrazole inhibitors for interleukin-2-inducible tyrosine kinase. Bioorganic and Medicinal Chemistry Letters, 22, 3296–3300.10.1016/j.bmcl.2012.03.016
   PubMed Web of Science ®Google Scholar
• Mouchlis, V. D., Melagraki, G., Mavromoustakos, T., Kollias, G., & Afantitis, A. (2012). Molecular modeling on pyrimidine-urea inhibitors of TNF-α production: An integrated approach using a combination of molecular docking, classification techniques, and 3D-QSAR CoMSIA. Journal of Chemical Information and Modeling, 52, 711–723.10.1021/ci200579f
   PubMed Web of Science ®Google Scholar
• Mullard, A. (2013). 2012 FDA drug approvals. Nature Reviews Drug Discovery, 12, 87–90.10.1038/nrd3946
   PubMed Web of Science ®Google Scholar
• PHASE. (2012). Version 3.4. New York, NY: Schrödinger, LLC.
   Google Scholar
• Pissot-Soldermann, C., Gerspacher, M., Furet, P., Gaul, C., Holzer, P., McCarthy, C., … Tavares, G. A. (2010). Discovery and SAR of potent, orally available 2, 8-diaryl-quinoxalines as a new class of JAK2 inhibitors. Bioorganic & Medicinal Chemistry Letters, 20, 2609–2613.10.1016/j.bmcl.2010.02.056
   PubMed Web of Science ®Google Scholar
• Prime. (2012). Version 3.1. New York, NY: Schrödinger, LLC.
   Google Scholar
• QikProp. (2012). Version 3.5. New York, NY: Schrödinger, LLC.
   Google Scholar
• Reddy, A. S., Pati, S. P., Kumar, P. P., Pradeep, H. N., & Sastry, G. N. (2007). Virtual screening in drug discovery – A computational perspective. Current Protein Peptide Science, 8, 329–351.10.2174/138920307781369427
   PubMed Web of Science ®Google Scholar
• Robak, T., & Robak, E. (2012). Tyrosine kinase inhibitors as potential drugs for B-cell lymphoid malignancies and autoimmune disorders. Expert Opinion on Investigational Drugs, 21, 921–947.10.1517/13543784.2012.685650
   PubMed Web of Science ®Google Scholar
• Rodems, S. M., Hamman, B. D., Lin, C., Zhao, J., Shah, S., Heidary, D., … Pollok, B. A. (2002). A FRET-based assay platform for ultra-high density drug screening of protein kinases and phosphatases. Assay and Drug Development Technologies, 1, 9–19.10.1089/154065802761001266
   PubMed Web of Science ®Google Scholar
• Roy, K., Das, R. N., Ambure, P., & Aher, R. B. (2016). Be aware of error measures. Further studies on validation of predictive QSAR models. Chemometrics and Intelligent Laboratory Systems, 152, 18–33.10.1016/j.chemolab.2016.01.008
   Web of Science ®Google Scholar
• Roy, K., Kar, S., & Ambure, P. (2015). On a simple approach for determining applicability domain of QSAR models. Chemometrics and Intelligent Laboratory Systems, 145, 22–29.10.1016/j.chemolab.2015.04.013
   Web of Science ®Google Scholar
• Roy, K., Kar, S., & Das, R. N. (2015). Understanding the basics of QSAR for applications in pharmaceutical sciences and risk assessment. Academic Press.
   Google Scholar
• Salam, N. K., Nuti, R., & Sherman, W. (2009). Novel method for generating structure-based pharmacophores using energetic analysis. Journal of Chemical Information and Modeling, 49, 2356–2368.10.1021/ci900212v
   PubMed Web of Science ®Google Scholar
• Sastry, G. M., Adzhigirey, M., Day, T., Annabhimoju, R., & Sherman, W. (2013). Protein and ligand preparation: Parameters, protocols, and influence on virtual screening enrichments. Journal of Computer Aided Molecular Design, 27, 221–234.10.1007/s10822-013-9644-8
   PubMed Web of Science ®Google Scholar
• Soth, M., Hermann, J. C., Yee, C., Alam, M., Barnett, J. W., Berry, P., … Vu, M. D. (2013). 3-amido pyrrolopyrazine JAK kinase inhibitors: Development of a JAK3 vs JAK1 selective inhibitor and evaluation in cellular and in vivo models. Journal of Medicinal Chemistry, 56, 345–356.10.1021/jm301646k
   PubMed Web of Science ®Google Scholar
• Tang, Q., Zhai, X., Tu, Y., Wang, P., Wang, L., Wu, C., … Zheng, P. (2016). Synthesis and antiproliferative activity of 6, 7-disubstituted-4-phenoxyquinoline derivatives bearing the 2-oxo-4-chloro-1, 2-dihydroquinoline-3-carboxamide moiety. Bioorganic and Medicinal Chemistry Letters, 26, 1794–1798.10.1016/j.bmcl.2016.02.037
   PubMed Web of Science ®Google Scholar
• Thoma, G., Blanz, J., Bühlmayer, P., Drückes, P., Kittelmann, M., Smith, A. B., … Liu, H. (2014). Syk inhibitors with potency in presence of blood. Bioorganic and Medicinal Chemistry Letters, 24, 2278–2282.10.1016/j.bmcl.2014.03.075
   PubMed Web of Science ®Google Scholar
• Thoma, G., Drückes, P., & Zerwes, H. G. (2014). Selective inhibitors of the Janus kinase Jak3 – Are they effective? Bioorganic and Medicinal Chemistry Letters, 24, 4617–4621.10.1016/j.bmcl.2014.08.046
   PubMed Web of Science ®Google Scholar
• Thoma, G., Nuninger, F., Falchetto, R., Hermes, E., Tavares, G. A., Vangrevelinghe, E., & Zerwes, H. G. (2011). Identification of a potent janus kinase 3 inhibitor with high selectivity within the janus kinase family. Journal of Medicinal Chemistry, 54, 284–288.10.1021/jm101157q
   PubMed Web of Science ®Google Scholar
• Verma, J., Khedkar, V. M., & Coutinho, E. C. (2010). 3D-QSAR in drug design – A review. Current Topics in Medicinal Chemistry, 10, 95–115.10.2174/156802610790232260
   PubMed Web of Science ®Google Scholar
• Weaver, S., & Gleeson, M. P. (2008). The importance of the domain of applicability in QSAR modeling. Journal of Molecular Graphics and Modelling, 26, 1315–1326.10.1016/j.jmgm.2008.01.002
   PubMed Web of Science ®Google Scholar
• Yang, S. M., Malaviya, R., Wilson, L. J., Argentieri, R., Chen, X., Yang, C., … Murray, W. V. (2007). Simplified staurosporine analogs as potent JAK3 inhibitors. Bioorganic and Medicinal Chemistry Letters, 17, 326–331.10.1016/j.bmcl.2006.10.062
   PubMed Web of Science ®Google Scholar
• Zhang, J. H., Chung, T. D., & Oldenburg, K. R. J. (1999). A Simple Statistical Parameter for Use in Evaluation and Validation of High Throughput Screening Assays. Journal of Biomolecular Screening, 4, 67–73.10.1177/108705719900400206
   PubMed Web of Science ®Google Scholar