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Synthesis and SAR of 1,9-dihydro-9-hydroxypyrazolo[3,4-b]quinolin-4-ones as novel, selective c-Jun N-terminal kinase inhibitors.

Liu M, Xin Z, Clampit JE, Wang S, Gum RJ, Haasch DL, Trevillyan JM, Abad-Zapatero C, Fry EH, Sham HL, Liu G
Bioorg Med Chem Lett 16 2590-4 (2006)
Cited: 30 times
EuropePMC logo PMID: 16527482

Abstract

A novel class of 1,9-dihydro-9-hydroxypyrazolo[3,4-b]quinolin-4-ones as c-Jun-N-terminal kinase (JNK) inhibitors is described. These compounds were synthesized via the condensation of 2-nitrobenzaldehydes and hydroxypyrazoles. The structure-activity relationships (SAR) and kinase selectivity profile of the inhibitors are also discussed. Compound 16 was identified as a potent JNK inhibitor with good cellular potency.

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Reviews citing this publication (4)

  1. Uses for JNK: the many and varied substrates of the c-Jun N-terminal kinases. Bogoyevitch MA, Kobe B. Microbiol Mol Biol Rev 70 1061-1095 (2006)
  2. Inhibitors of c-Jun N-terminal kinases: JuNK no more? Bogoyevitch MA, Arthur PG. Biochim Biophys Acta 1784 76-93 (2008)
  3. The role of cellular senescence in Werner syndrome: toward therapeutic intervention in human premature aging. Davis T, Wyllie FS, Rokicki MJ, Bagley MC, Kipling D. Ann N Y Acad Sci 1100 455-469 (2007)
  4. 1H-Pyrazolo[3,4-b]quinolines: Synthesis and Properties over 100 Years of Research. Danel A, Gondek E, Kucharek M, Szlachcic P, Gut A. Molecules 27 2775 (2022)

Articles citing this publication (6)

  1. Analysis of conditions affecting auto-phosphorylation of human kinases during expression in bacteria. Shrestha A, Hamilton G, O'Neill E, Knapp S, Elkins JM. Protein Expr Purif 81 136-143 (2012)
  2. Discovery of a new class of 4-anilinopyrimidines as potent c-Jun N-terminal kinase inhibitors: Synthesis and SAR studies. Liu M, Wang S, Clampit JE, Gum RJ, Haasch DL, Rondinone CM, Trevillyan JM, Abad-Zapatero C, Fry EH, Sham HL, Liu G. Bioorg Med Chem Lett 17 668-672 (2007)
  3. Discovery, synthesis and biological evaluation of isoquinolones as novel and highly selective JNK inhibitors (2). Asano Y, Kitamura S, Ohra T, Itoh F, Kajino M, Tamura T, Kaneko M, Ikeda S, Igata H, Kawamoto T, Sogabe S, Matsumoto S, Tanaka T, Yamaguchi M, Kimura H, Fukumoto S. Bioorg Med Chem 16 4699-4714 (2008)
  4. Synthesis and SAR of aminopyrimidines as novel c-Jun N-terminal kinase (JNK) inhibitors. Alam M, Beevers RE, Ceska T, Davenport RJ, Dickson KM, Fortunato M, Gowers L, Haughan AF, James LA, Jones MW, Kinsella N, Lowe C, Meissner JW, Nicolas AL, Perry BG, Phillips DJ, Pitt WR, Platt A, Ratcliffe AJ, Sharpe A, Tait LJ. Bioorg Med Chem Lett 17 3463-3467 (2007)
  5. Synthesis and SAR of 4-substituted-2-aminopyrimidines as novel c-Jun N-terminal kinase (JNK) inhibitors. Humphries PS, Lafontaine JA, Agree CS, Alexander D, Chen P, Do QQ, Li LY, Lunney EA, Rajapakse RJ, Siegel K, Timofeevski SL, Wang T, Wilhite DM. Bioorg Med Chem Lett 19 2099-2102 (2009)
  6. Discovery of Novel c-Jun N-Terminal Kinase 1 Inhibitors from Natural Products: Integrating Artificial Intelligence with Structure-Based Virtual Screening and Biological Evaluation. Yang R, Zhao G, Yan B. Molecules 27 6249 (2022)


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