Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases

C. C. Thinnes, A. Tumber, C. Yapp, G. Scozzafava, T. Yeh, M. C. Chan, T. A. Tran, K. Hsu, H. Tarhonskaya, L. J. Walport, S. E. Wilkins, E. D. Martinez, S. Müller, C. W. Pugh, P. J. Ratcliffe, P. E. Brennan, A. Kawamura, C. J. Schofield

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

There is interest in developing potent, selective, and cell-permeable inhibitors of human ferrous iron and 2-oxoglutarate (2OG) oxygenases for use in functional and target validation studies. The 3-component Betti reaction enables efficient one-step C-7 functionalisation of modified 8-hydroxyquinolines (8HQs) to produce cell-active inhibitors of KDM4 histone demethylases and other 2OG oxygenases; the work exemplifies how a template-based metallo-enzyme inhibitor approach can be used to give biologically active compounds.

Original languageEnglish (US)
Pages (from-to)15458-15461
Number of pages4
JournalChemical Communications
Volume51
Issue number84
DOIs
StatePublished - 2015

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Ceramics and Composites
  • Electronic, Optical and Magnetic Materials
  • Surfaces, Coatings and Films
  • Materials Chemistry
  • Metals and Alloys

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    Thinnes, C. C., Tumber, A., Yapp, C., Scozzafava, G., Yeh, T., Chan, M. C., Tran, T. A., Hsu, K., Tarhonskaya, H., Walport, L. J., Wilkins, S. E., Martinez, E. D., Müller, S., Pugh, C. W., Ratcliffe, P. J., Brennan, P. E., Kawamura, A., & Schofield, C. J. (2015). Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases. Chemical Communications, 51(84), 15458-15461. https://doi.org/10.1039/c5cc06095h