Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere

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  • Benjamin A. Chalmers
    School of Chemistry and Molecular Biosciences University of Queensland (UQ) Brisbane 4072 Queensland (QLD Australia
  • Hui Xing
    School of Chemistry and Molecular Biosciences University of Queensland (UQ) Brisbane 4072 Queensland (QLD Australia
  • Sevan Houston
    School of Chemistry and Molecular Biosciences University of Queensland (UQ) Brisbane 4072 Queensland (QLD Australia
  • Charlotte Clark
    Queensland Brain Institute, UQ Australia
  • Sussan Ghassabian
    Centre for Integrated Preclinical Drug Development, UQ Australia
  • Andy Kuo
    Centre for Integrated Preclinical Drug Development, UQ Australia
  • Benjamin Cao
    CISRO Manufacturing Ian Wark Laboratory Melbourne 3168 Victoria (VIC Australia
  • Andrea Reitsma
    CISRO Manufacturing Ian Wark Laboratory Melbourne 3168 Victoria (VIC Australia
  • Cody‐Ellen P. Murray
    School of Biological Sciences, UQ Australia
  • Jeanette E. Stok
    School of Chemistry and Molecular Biosciences University of Queensland (UQ) Brisbane 4072 Queensland (QLD Australia
  • Glen M. Boyle
    QIMR Berghofer Medical Research Institute PO Royal Brisbane Hospital Brisbane 4029 QLD Australia
  • Carly J. Pierce
    QIMR Berghofer Medical Research Institute PO Royal Brisbane Hospital Brisbane 4029 QLD Australia
  • Stuart W. Littler
    CISRO Manufacturing Ian Wark Laboratory Melbourne 3168 Victoria (VIC Australia
  • David A. Winkler
    CISRO Manufacturing Ian Wark Laboratory Melbourne 3168 Victoria (VIC Australia
  • Paul V. Bernhardt
    School of Chemistry and Molecular Biosciences University of Queensland (UQ) Brisbane 4072 Queensland (QLD Australia
  • Cielo Pasay
    QIMR Berghofer Medical Research Institute PO Royal Brisbane Hospital Brisbane 4029 QLD Australia
  • James J. De Voss
    School of Chemistry and Molecular Biosciences University of Queensland (UQ) Brisbane 4072 Queensland (QLD Australia
  • James McCarthy
    QIMR Berghofer Medical Research Institute PO Royal Brisbane Hospital Brisbane 4029 QLD Australia
  • Peter G. Parsons
    QIMR Berghofer Medical Research Institute PO Royal Brisbane Hospital Brisbane 4029 QLD Australia
  • Gimme H. Walter
    School of Biological Sciences, UQ Australia
  • Maree T. Smith
    Centre for Integrated Preclinical Drug Development, UQ Australia
  • Helen M. Cooper
    Queensland Brain Institute, UQ Australia
  • Susan K. Nilsson
    CISRO Manufacturing Ian Wark Laboratory Melbourne 3168 Victoria (VIC Australia
  • John Tsanaktsidis
    CISRO Manufacturing Ian Wark Laboratory Melbourne 3168 Victoria (VIC Australia
  • G. Paul Savage
    CISRO Manufacturing Ian Wark Laboratory Melbourne 3168 Victoria (VIC Australia
  • Craig M. Williams
    School of Chemistry and Molecular Biosciences University of Queensland (UQ) Brisbane 4072 Queensland (QLD Australia

書誌事項

公開日
2016-02-05
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#am
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/anie.201510675
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>Pharmaceutical and agrochemical discovery programs are under considerable pressure to meet increasing global demand and thus require constant innovation. Classical hydrocarbon scaffolds have long assisted in bringing new molecules to the market place, but an obvious omission is that of the Platonic solid cubane. Eaton, however, suggested that this molecule has the potential to act as a benzene bioisostere. Herein, we report the validation of Eaton's hypothesis with cubane derivatives of five molecules that are used clinically or as agrochemicals. Two cubane analogues showed increased bioactivity compared to their benzene counterparts whereas two further analogues displayed equal bioactivity, and the fifth one demonstrated only partial efficacy. Ramifications from this study are best realized by reflecting on the number of bioactive molecules that contain a benzene ring. Substitution with the cubane scaffold where possible could revitalize these systems, and thus expedite much needed lead candidate identification.</jats:p>

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