Pharmacophore generation and atom-based 3D-QSAR of novel quinoline-3-carbonitrile derivatives as Tpl2 kinase inhibitors

References

• Das S, Cho J, Lambertz I, Kelliher MA, Eliopoulos AG, Du K et al. Tpl2/cot signals activate ERK, JNK, and NF-kappaB in a cell-type and stimulus-specific manner. J Biol Chem 2005;280:23748–23757.
   PubMedGoogle Scholar
• Dumitru CD, Ceci JD, Tsatsanis C, Kontoyiannis D, Stamatakis K, Lin JH et al. TNF-alpha induction by LPS is regulated posttranscriptionally via a Tpl2/ERK-dependent pathway. Cell 2000;103:1071–1083.
   PubMed Web of Science ®Google Scholar
• Eliopoulos AG, Dumitru CD, Wang CC, Cho J, Tsichlis PN. Induction of COX-2 by LPS in macrophages is regulated by Tpl2-dependent CREB activation signals. Embo J 2002;21:4831–4840.
   PubMed Web of Science ®Google Scholar
• Eliopoulos AG, Wang CC, Dumitru CD, Tsichlis PN. Tpl2 transduces CD40 and TNF signals that activate ERK and regulates IgE induction by CD40. Embo J 2003;22:3855–3864.
   PubMed Web of Science ®Google Scholar
• Kontoyiannis D, Boulougouris G, Manoloukos M, Armaka M, Apostolaki M, Pizarro T et al. Genetic dissection of the cellular pathways and signaling mechanisms in modeled tumor necrosis factor-induced Crohn’s-like inflammatory bowel disease. J Exp Med 2002;196:1563–1574.
   PubMed Web of Science ®Google Scholar
• Rodríguez C, Pozo M, Nieto E, Fernández M, Alemany S. TRAF6 and Src kinase activity regulates Cot activation by IL-1. Cell Signal 2006;18:1376–1385.
   PubMedGoogle Scholar
• Stafford MJ, Morrice NA, Peggie MW, Cohen P. Interleukin-1 stimulated activation of the COT catalytic subunit through the phosphorylation of Thr290 and Ser62. FEBS Lett 2006;580:4010–4014.
   PubMedGoogle Scholar
• Sugimoto K, Ohata M, Miyoshi J, Ishizaki H, Tsuboi N, Masuda A et al. A serine/threonine kinase, Cot/Tpl2, modulates bacterial DNA-induced IL-12 production and Th cell differentiation. J Clin Invest 2004;114:857–866.
   PubMedGoogle Scholar
• Choy EH, Panayi GS. Cytokine pathways and joint inflammation in rheumatoid arthritis. N Engl J Med 2001;344:907–916.
   PubMed Web of Science ®Google Scholar
• Aggarwal BB, Samanta A, Feldmann MA. Compendium of Cytokines and Other Mediators of Host Defense. Academic Press, San Diego 2001: pp. 413–434.
   Google Scholar
• Feldmann M, Maini RN. Anti-TNF alpha therapy of rheumatoid arthritis: What have we learned? Annu Rev Immunol 2001;19:163–196.
   PubMed Web of Science ®Google Scholar
• Schottelius AJ, Moldawer LL, Dinarello CA, Asadullah K, Sterry W, Edwards CK 3rd. Biology of tumor necrosis factor-alpha- implications for psoriasis. Exp Dermatol 2004;13:193–222.
   PubMed Web of Science ®Google Scholar
• Simmons DL. What makes a good anti-inflammatory drug target? Drug Discov Today 2006;11:210–219.
   PubMed Web of Science ®Google Scholar
• Doran MF, Pond GR, Crowson CS, O’Fallon WM, Gabriel SE. Trends in incidence and mortality in rheumatoid arthritis in Rochester, Minnesota, over a forty-year period. Arthritis Rheum 2002;46:625–631.
   PubMed Web of Science ®Google Scholar
• Smyth A, Houlihan DD, Tuite H, Fleming C, O’Gorman TA. Necrotising fasciitis of the shoulder in association with rheumatoid arthritis treated with etanercept: A case report. J Med Case Reports 2010;4:367.
   PubMedGoogle Scholar
• Gutierrez M, Becciolini A, Bertolazzi C, Di Geso L, Tardella M, Ariani A et al. [Polyarthritis flare in patient with ankylosing spondylitis treated with infliximab]. Reumatismo 2010;62:221–224.
   PubMedGoogle Scholar
• Shenoi S, Wallace CA. Tumor necrosis factor inhibitors in the management of juvenile idiopathic arthritis: An evidence-based review. Paediatr Drugs 2010;12:367–377.
   PubMedGoogle Scholar
• Hu Y, Green N, Gavrin LK, Janz K, Kaila N, Li HQ et al. Inhibition of Tpl2 kinase and TNFalpha production with quinoline-3-carbonitriles for the treatment of rheumatoid arthritis. Bioorg Med Chem Lett 2006;16:6067–6072.
   PubMed Web of Science ®Google Scholar
• Hall JP, Kurdi Y, Hsu S, Cuozzo J, Liu J, Telliez JB et al. Pharmacologic inhibition of tpl2 blocks inflammatory responses in primary human monocytes, synoviocytes, and blood. J Biol Chem 2007;282:33295–33304.
   PubMed Web of Science ®Google Scholar
• Green N, Hu Y, Janz K, Li HQ, Kaila N, Guler S et al. Inhibitors of tumor progression loci-2 (Tpl2) kinase and tumor necrosis factor alpha (TNF-alpha) production: Selectivity and in vivo antiinflammatory activity of novel 8-substituted-4-anilino-6-aminoquinoline-3-carbonitriles. J Med Chem 2007;50:4728–4745.
   PubMed Web of Science ®Google Scholar
• Caivano M, Rodriguez C, Cohen P, Alemany S. 15-Deoxy-Delta12,14-prostaglandin J2 regulates endogenous Cot MAPK kinase kinase 1 activity induced by lipopolysaccharide. J Biol Chem 2003;278:52124–52130.
   PubMedGoogle Scholar
• Gavrin LK, Green N, Hu Y, Janz K, Kaila N, Li HQ et al. Inhibition of Tpl2 kinase and TNF-alpha production with 1,7-naphthyridine-3-carbonitriles: Synthesis and structure-activity relationships. Bioorg Med Chem Lett 2005;15:5288–5292.
   PubMed Web of Science ®Google Scholar
• Kaila N, Green N, Li HQ, Hu Y, Janz K, Gavrin LK et al. Identification of a novel class of selective Tpl2 kinase inhibitors: 4-Alkylamino-[1,7]naphthyridine-3-carbonitriles. Bioorg Med Chem 2007;15:6425–6442.
   PubMed Web of Science ®Google Scholar
• Wu J, Green N, Hotchandani R, Hu Y, Condon J, Huang A et al. Selective inhibitors of tumor progression loci-2 (Tpl2) kinase with potent inhibition of TNF-alpha production in human whole blood. Bioorg Med Chem Lett 2009;19:3485–3488.
   PubMed Web of Science ®Google Scholar
• Mahipal Tanwar, OP, Karthikeyan C, Moorthy NS, Trivedi P. 3D QSAR of Aminophenyl Benzamide Derivatives as Histone Deacetylase Inhibitors. Med Chem 2010;6:287–285.
   Google Scholar
• Samantha L, Cesare M, Aleksey K, Mattia S, Stefano M, Elena C, Dorotea R, Alessandro C. SAR and QSAR study on 2-aminothiazole derivatives, modulators of transcriptional repression in Huntington’s disease. Bioorg Med Chem Lett 2008;16:5695–5703.
   Google Scholar
• User manual Phase, version 3.0, Schrödinger, LLC, New York, NY, 2008.
   Google Scholar
• Shah UA, Deokar HS, Kadam SS, Kulkarni VM. Pharmacophore generation and atom-based 3D-QSAR of novel 2-(4-methylsulfonylphenyl)pyrimidines as COX-2 inhibitors. Mol Divers 2010;14:559–568.
   PubMed Web of Science ®Google Scholar
• Dixon SL, Smondyrev AM, Knoll EH, Rao SN, Shaw DE, Friesner RA. PHASE: A new engine for pharmacophore perception, 3D QSAR model development, and 3D database screening: 1. Methodology and preliminary results. J Comput Aided Mol Des 2006;20:647–671.
   PubMed Web of Science ®Google Scholar
• Eng J. Receiver operating characteristic analysis: A primer. Acad Radiol 2005;12:909–916.
   PubMed Web of Science ®Google Scholar