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

doi:10.1039/c5cc06095h

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 journal › Article › peer-review

33 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 language	English (US)
Pages (from-to)	15458-15461
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	84
DOIs	https://doi.org/10.1039/c5cc06095h
State	Published - 2015

ASJC Scopus subject areas

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

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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

Thinnes, CC, Tumber, A, Yapp, C, Scozzafava, G, Yeh, T, Chan, MC, Tran, TA, Hsu, K, Tarhonskaya, H, Walport, LJ, Wilkins, SE, Martinez, ED, Müller, S, Pugh, CW, Ratcliffe, PJ, Brennan, PE, Kawamura, A & Schofield, CJ 2015, 'Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases', Chemical Communications, vol. 51, no. 84, pp. 15458-15461. https://doi.org/10.1039/c5cc06095h

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title = "Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases",

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.",

author = "Thinnes, {C. C.} and A. Tumber and C. Yapp and G. Scozzafava and T. Yeh and Chan, {M. C.} and Tran, {T. A.} and K. Hsu and H. Tarhonskaya and Walport, {L. J.} and Wilkins, {S. E.} and Martinez, {E. D.} and S. M{\"u}ller and Pugh, {C. W.} and Ratcliffe, {P. J.} and Brennan, {P. E.} and A. Kawamura and Schofield, {C. J.}",

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year = "2015",

doi = "10.1039/c5cc06095h",

language = "English (US)",

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AU - Thinnes, C. C.

AU - Tumber, A.

AU - Yapp, C.

AU - Scozzafava, G.

AU - Yeh, T.

AU - Chan, M. C.

AU - Tran, T. A.

AU - Hsu, K.

AU - Tarhonskaya, H.

AU - Walport, L. J.

AU - Wilkins, S. E.

AU - Martinez, E. D.

AU - Müller, S.

AU - Pugh, C. W.

AU - Ratcliffe, P. J.

AU - Brennan, P. E.

AU - Kawamura, A.

AU - Schofield, C. J.

PY - 2015

Y1 - 2015

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AB - 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.

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

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