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Volumn 49, Issue 10, 2006, Pages 2898-2908

Evolution of the thienopyridine class of inhibitors of IκB kinase-β: Part I: Hit-to-lead strategies

Author keywords

[No Author keywords available]

Indexed keywords

I KAPPA B KINASE BETA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; THIOPHENE DERIVATIVE;

EID: 33646751327     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0510979     Document Type: Article
Times cited : (70)

References (53)
  • 2
    • 0037323146 scopus 로고    scopus 로고
    • Lead generation-enhancing the success of drug discovery by investing in the hit to lead process
    • (b) Alanine, A.; Nettekoven, M.; Roberts, E.; Thomas, A. W. Lead generation-enhancing the success of drug discovery by investing in the hit to lead process. Comb. Chem. High Throughput Screening 2003, 6, 51-66.
    • (2003) Comb. Chem. High Throughput Screening , vol.6 , pp. 51-66
    • Alanine, A.1    Nettekoven, M.2    Roberts, E.3    Thomas, A.W.4
  • 3
    • 6444230439 scopus 로고    scopus 로고
    • Lead generation: Sowing the seeds for future success
    • (c) Bleicher, K. H.; Nettekoven, M.; Peters, J.-U.; Wyler, R. Lead generation: sowing the seeds for future success. Chimia 2004, 58, 588-600.
    • (2004) Chimia , vol.58 , pp. 588-600
    • Bleicher, K.H.1    Nettekoven, M.2    Peters, J.-U.3    Wyler, R.4
  • 4
    • 0001871136 scopus 로고    scopus 로고
    • Hit-to-lead chemistry: A key element in new lead generation
    • (d) Michne, W. F. Hit-to-lead chemistry: A key element in new lead generation. Pharm. News 1996, 3, 19-21.
    • (1996) Pharm. News , vol.3 , pp. 19-21
    • Michne, W.F.1
  • 5
    • 0037124196 scopus 로고    scopus 로고
    • Drugs, leads, and drug-likeness: An analysis of some recently launched drugs
    • Proudfoot, J. R. Drugs, leads, and drug-likeness: An analysis of some recently launched drugs. Bioorg. Med. Chem. Lett. 2002, 12, 1647-1650.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1647-1650
    • Proudfoot, J.R.1
  • 6
    • 0033595893 scopus 로고    scopus 로고
    • How NF-κB is activated: The role of the IκB kinase (IKK) complex
    • (a) Karin, M. How NF-κB is activated: The role of the IκB kinase (IKK) complex. Oncogene 1999, 18, 6867-6874.
    • (1999) Oncogene , vol.18 , pp. 6867-6874
    • Karin, M.1
  • 7
    • 0033600604 scopus 로고    scopus 로고
    • The beginning of the end: IκB kinase (IKK) and NF-κB activation
    • (b) Karin, M. The beginning of the end: IκB kinase (IKK) and NF-κB activation. J. Biol. Chem. 1999, 274, 27339-27342.
    • (1999) J. Biol. Chem. , vol.274 , pp. 27339-27342
    • Karin, M.1
  • 8
    • 0034746919 scopus 로고    scopus 로고
    • NF-κB: A key role in inflammatory diseases
    • (c) Tak, P. P.; Firestein, G. S. NF-κB: A key role in inflammatory diseases. J. Clin. Invest. 2001, 107, 7-11.
    • (2001) J. Clin. Invest. , vol.107 , pp. 7-11
    • Tak, P.P.1    Firestein, G.S.2
  • 9
    • 0346505340 scopus 로고    scopus 로고
    • The IKK NF-κB system: A treasure trove for drug development
    • (d) Karin, M.; Yamamoto, Y.; Wang, Q. M. The IKK NF-κB system: A treasure trove for drug development. Nat. Rev. Drug Discovery 2004, 3, 17-26.
    • (2004) Nat. Rev. Drug Discovery , vol.3 , pp. 17-26
    • Karin, M.1    Yamamoto, Y.2    Wang, Q.M.3
  • 11
    • 14644427890 scopus 로고    scopus 로고
    • Local and systemic insulin resistance resulting from hepatic activation of IKK-β and NF-κB
    • (f) Cai, D.; Yuan, M.; Frantz, D.; Melendez, P. A.; Hansen, L.; Lee, J.; Shoelson, S. E. Local and systemic insulin resistance resulting from hepatic activation of IKK-β and NF-κB. Nat. Med. 2005, 11, 183-190.
    • (2005) Nat. Med. , vol.11 , pp. 183-190
    • Cai, D.1    Yuan, M.2    Frantz, D.3    Melendez, P.A.4    Hansen, L.5    Lee, J.6    Shoelson, S.E.7
  • 12
    • 0030271387 scopus 로고    scopus 로고
    • NF-κB: Ten years after
    • (a) Baeuerle, P. A.; Baltimore, D. NF-κB: Ten years after. Cell 1996, 87, 13-20.
    • (1996) Cell , vol.87 , pp. 13-20
    • Baeuerle, P.A.1    Baltimore, D.2
  • 14
    • 0036605858 scopus 로고    scopus 로고
    • Small-molecule inhibitors of NF-κB for the treatment of inflammatory joint disease
    • Roshak, A. K.; Callahan, J. F.; Blake, S. M. Small-molecule inhibitors of NF-κB for the treatment of inflammatory joint disease. Curr. Opin. Pharmacol. 2002, 2, 316-321. Abbreviations used in this section: IL (interleukin); TNF (tumor necrosis factor); LPS (lipopolysaccharide); MCP (monocyte/macrophage chemoattractant protein); RANTES (regulated on activation, normal T-cell expressed and secreted); ICAM (intercellular adhesion molecule); VCAM (vascular cell adhesion molecule); COX (cyclooxygenase); iNOS (inducible nitric oxide synthase); MMP (matrix metalloproteinase).
    • (2002) Curr. Opin. Pharmacol. , vol.2 , pp. 316-321
    • Roshak, A.K.1    Callahan, J.F.2    Blake, S.M.3
  • 15
    • 0033996762 scopus 로고    scopus 로고
    • The IκB kinase (IKK) and NF-κB: Key elements of proinflammatory signaling
    • Karin, M.; Delhase, M. The IκB kinase (IKK) and NF-κB: key elements of proinflammatory signaling. Semin. Immunol. 2000, 12, 85-98.
    • (2000) Semin. Immunol. , vol.12 , pp. 85-98
    • Karin, M.1    Delhase, M.2
  • 16
    • 0033537719 scopus 로고    scopus 로고
    • Positive and negative regulation of IκB kinase activity through IKKβ subunit phosphorylation
    • Delhause, M.; Hayakawa, M.; Chen, Y.; Karin, M. Positive and negative regulation of IκB kinase activity through IKKβ subunit phosphorylation. Science 1999, 284, 309-313.
    • (1999) Science , vol.284 , pp. 309-313
    • Delhause, M.1    Hayakawa, M.2    Chen, Y.3    Karin, M.4
  • 17
    • 0033537767 scopus 로고    scopus 로고
    • Abnormal morphogenesis but intact IKK activation in mice lacking the IKKα subunit of IκB kinase
    • Hu, Y.; Baud, V.; Delhase, M.; Zhang, P.; Deerinck, T.; Ellisman, M.; Johnson, R.; Karin, M. Abnormal morphogenesis but intact IKK activation in mice lacking the IKKα subunit of IκB kinase. Science 1999, 284, 316-320.
    • (1999) Science , vol.284 , pp. 316-320
    • Hu, Y.1    Baud, V.2    Delhase, M.3    Zhang, P.4    Deerinck, T.5    Ellisman, M.6    Johnson, R.7    Karin, M.8
  • 18
    • 0033537739 scopus 로고    scopus 로고
    • Severe liver degeneration in mice lacking the IκB kinase 2 gene
    • Li, Q.; Van Antwerp, D.; Mercurio, F.; Lee, K.-F.; Verma, I. M. Severe liver degeneration in mice lacking the IκB kinase 2 gene. Science 1999, 284, 321-325.
    • (1999) Science , vol.284 , pp. 321-325
    • Li, Q.1    Van Antwerp, D.2    Mercurio, F.3    Lee, K.-F.4    Verma, I.M.5
  • 19
    • 0037061628 scopus 로고    scopus 로고
    • A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening
    • For a description of one mechanism of compound promiscuity see: McGovern, S. L.; Caselli, E.; Grigorieff, N.; Shoichet, B. K. A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. J. Med. Chem.2002, 45, 1712-1722.
    • (2002) J. Med. Chem. , vol.45 , pp. 1712-1722
    • McGovern, S.L.1    Caselli, E.2    Grigorieff, N.3    Shoichet, B.K.4
  • 20
    • 0030756360 scopus 로고    scopus 로고
    • Reactive compounds and in vitro false positives in HTS
    • (a) Rishton, G. M. Reactive compounds and in vitro false positives in HTS. Drug Discover Today 1997, 2, 382-384.
    • (1997) Drug Discover Today , vol.2 , pp. 382-384
    • Rishton, G.M.1
  • 21
    • 0037439447 scopus 로고    scopus 로고
    • Nonleadlikeness and leadlikeness in biochemical screening
    • See also 1a for more examples of structural filters
    • (b) Rishton, G. M. Nonleadlikeness and leadlikeness in biochemical screening. Drug Discovery Today 2003, 8, 86-96. See also 1a for more examples of structural filters.
    • (2003) Drug Discovery Today , vol.8 , pp. 86-96
    • Rishton, G.M.1
  • 22
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • (a) Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 1997, 23, 3-25.
    • (1997) Adv. Drug Deliv. Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 23
    • 0033179183 scopus 로고    scopus 로고
    • Recognizing molecules with drug-like properties
    • (b) Walters, W. P.; Ajay; Murcko, M. A. Recognizing molecules with drug-like properties. Curr. Opin. Chem. Biol. 1999, 3, 384-87.
    • (1999) Curr. Opin. Chem. Biol. , vol.3 , pp. 384-387
    • Walters, W.P.1    Ajay2    Murcko, M.A.3
  • 25
    • 0033981358 scopus 로고    scopus 로고
    • Computational methods for the prediction of 'drug-likeness'
    • (d) Clark, D. E.; Pickett, S. D. Computational methods for the prediction of 'drug-likeness'. Drug Discovery Today 2000, 5, 49-58.
    • (2000) Drug Discovery Today , vol.5 , pp. 49-58
    • Clark, D.E.1    Pickett, S.D.2
  • 26
    • 0037404468 scopus 로고    scopus 로고
    • Selection criteria for drug-like compounds
    • (e) Muegge, I. Selection criteria for drug-like compounds. Med. Res. Rev. 2003, 23, 302-321.
    • (2003) Med. Res. Rev. , vol.23 , pp. 302-321
    • Muegge, I.1
  • 27
    • 0033576601 scopus 로고    scopus 로고
    • The design of leadlike combinatorial libraries
    • For a more stringent property assessment describing "lead-like" characteristics see: (f) Teague, S. J.; Davis, A. M.; Leeson, P. D.; Oprea, T. The Design of Leadlike Combinatorial Libraries. Angew. Chem., Int. Ed. 1999, 38, 3743-3748.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 3743-3748
    • Teague, S.J.1    Davis, A.M.2    Leeson, P.D.3    Oprea, T.4
  • 28
    • 0035438391 scopus 로고    scopus 로고
    • Is there a difference between leads and drugs? A historical perspective
    • (g) Oprea, T. I.; Davis, A. M.; Teague, S. J.; Leeson, P. D. Is there a difference between leads and drugs? A historical perspective. J. Chem. Inf. Comput. Sci. 2001, 41, 1308-1315.
    • (2001) J. Chem. Inf. Comput. Sci. , vol.41 , pp. 1308-1315
    • Oprea, T.I.1    Davis, A.M.2    Teague, S.J.3    Leeson, P.D.4
  • 36
    • 0003734635 scopus 로고    scopus 로고
    • Accelrys Inc.: San Diego, CA
    • Catalyst, version 4.0; Accelrys Inc.: San Diego, CA.
    • Catalyst, Version 4.0
  • 37
    • 1642270826 scopus 로고    scopus 로고
    • Recent kinase and kinase inhibitor X-ray structures: Mechanisms of inhibition and selectivity insights
    • For recent references to structural information for kinase inhibitors see Cherry, M.; Williams, D. H. Recent kinase and kinase inhibitor X-ray structures: Mechanisms of inhibition and selectivity insights. Curr. Med. Chem. 2004, 11, 663-673.
    • (2004) Curr. Med. Chem. , vol.11 , pp. 663-673
    • Cherry, M.1    Williams, D.H.2
  • 38
    • 84954208573 scopus 로고    scopus 로고
    • Structural aspects of kinases and their inhibitors
    • Kubinyi, H., Muller, G., Eds.; Wiley-VCH: New York
    • (b) Buijsman, R. Structural aspects of kinases and their inhibitors. In Chemogenomics in Drug Discover); Kubinyi, H., Muller, G., Eds.; Wiley-VCH: New York, 2004; Vol. 22, pp 191-217.
    • (2004) Chemogenomics in Drug Discover , vol.22 , pp. 191-217
    • Buijsman, R.1
  • 39
    • 0008702436 scopus 로고
    • Preparation of 2-alkyl- and 2-aryl-5-amino-4-cyano-1,3-oxazoles
    • Freeman, F.; Kim, D. S. H. L. Preparation of 2-alkyl- and 2-aryl-5-amino-4-cyano-1,3-oxazoles. Tetrahedron Lett. 1989, 2631-2632.
    • (1989) Tetrahedron Lett. , pp. 2631-2632
    • Freeman, F.1    Kim, D.S.H.L.2
  • 44
    • 24944497371 scopus 로고    scopus 로고
    • Features of selective kinase inhibitors
    • (a) Knight, Z. A.; Shokat, K. M. Features of selective kinase inhibitors. Chem. Biol. 2005, 12, 621-637.
    • (2005) Chem. Biol. , vol.12 , pp. 621-637
    • Knight, Z.A.1    Shokat, K.M.2
  • 45
    • 0031887743 scopus 로고    scopus 로고
    • Protein kinase inhibitors: The tyrosine-specific protein kinases
    • (b) Lawrence, D.; Niu, J. Protein kinase inhibitors: The tyrosine-specific protein kinases. Pharmacol. Ther. 1998, 77, 81-114.
    • (1998) Pharmacol. Ther. , vol.77 , pp. 81-114
    • Lawrence, D.1    Niu, J.2
  • 46
    • 0034461768 scopus 로고    scopus 로고
    • Drug-like properties and the causes of poor solubility and poor permeability
    • Lipinski, C. A. Drug-like properties and the causes of poor solubility and poor permeability. J. Pharmacol. Toxicol. Methods 2000, 44, 235-249.
    • (2000) J. Pharmacol. Toxicol. Methods , vol.44 , pp. 235-249
    • Lipinski, C.A.1
  • 47
    • 0031781430 scopus 로고    scopus 로고
    • Correlating partitioning and caco-2 cell permeability of structurally diverse small molecular weight compounds
    • Yazdanian, M.; Glynn S. L.; Wright, J. L.; Hawi, A. Correlating partitioning and caco-2 cell permeability of structurally diverse small molecular weight compounds. Pharm. Res. 1998, 15, 1490-1494.
    • (1998) Pharm. Res. , vol.15 , pp. 1490-1494
    • Yazdanian, M.1    Glynn, S.L.2    Wright, J.L.3    Hawi, A.4
  • 48
    • 33646745188 scopus 로고    scopus 로고
    • Microsomal stability data generated at Cerep, Inc.
    • Microsomal stability data generated at Cerep, Inc.
  • 49
    • 0034460075 scopus 로고    scopus 로고
    • Fluorometric screening for metabolism-based drug-drug interactions
    • Crespi, C. L., Stresser, D. M. Fluorometric screening for metabolism-based drug-drug interactions. J. Pharmacol. Toxicol. Methods 2000, 44, 325-331.
    • (2000) J. Pharmacol. Toxicol. Methods , vol.44 , pp. 325-331
    • Crespi, C.L.1    Stresser, D.M.2
  • 50
    • 33646747702 scopus 로고    scopus 로고
    • note
    • (a) Biosource, DAL1100 was used according to the manufacturer's instructions to assess cell toxicity in HeLa.
  • 51
    • 0033856957 scopus 로고    scopus 로고
    • Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity
    • (b) O'Brien, J.; Wilson, I.; Orton, T.; Pognan, F. Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity. Eur. J. Biochem. 2000, 267, 5421-5426.
    • (2000) Eur. J. Biochem. , vol.267 , pp. 5421-5426
    • O'Brien, J.1    Wilson, I.2    Orton, T.3    Pognan, F.4
  • 52
    • 0031852098 scopus 로고    scopus 로고
    • A novel one-step, highly sensitive fluorometric assay to evaluate cell-mediated cytotoxicity
    • (c) Nociari, M. M.; Shalev, A.; Benias, P.; Russo, C. A novel one-step, highly sensitive fluorometric assay to evaluate cell-mediated cytotoxicity. J. Immunol. Methods 1998, 213, 157-67.
    • (1998) J. Immunol. Methods , vol.213 , pp. 157-167
    • Nociari, M.M.1    Shalev, A.2    Benias, P.3    Russo, C.4
  • 53
    • 33646734099 scopus 로고    scopus 로고
    • to be submitted for publication
    • Wu, J.-P. et al., to be submitted for publication.
    • Wu, J.-P.1


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