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SYNTHETIC METHODOLOGY

Simple strategy towards amide bioisosteres

Aryl aminooxetanes are used as amide bioisosteres in drug discovery but there are limited strategies for synthesizing them. Now, an approach has been developed that simplifies the synthesis of these privileged motifs, enabling a broad range of amines to be used.

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Fig. 1: The synthesis of aryl aminooxetanes.

References

  1. Meanwell, N. A. J. Med. Chem. 54, 2529–2591 (2011).

    Article  CAS  Google Scholar 

  2. Kumari, S., Carmona, A. V., Tiwari, A. K. & Trippier, P. C. J. Med. Chem. 63, 12290–12358 (2020).

    Article  CAS  Google Scholar 

  3. Bull, J. A., Croft, R. A., Davis, O. A., Doran, R. & Morgan, K. F. Chem. Rev. 116, 12150–12233 (2016).

    Article  CAS  Google Scholar 

  4. Delost, M. D., Smith, D. T., Anderson, B. J. & Njardarson, J. T. J. Med. Chem. 61, 10996–11020 (2018).

    Article  CAS  Google Scholar 

  5. Rojas, J. J. et al. Nat. Chem. https://doi.org/10.1038/s41557-021-00856-2 (2022).

  6. Hamzik, P. J. & Brubaker, J. D. Org. Lett. 12, 1116–1119 (2010).

    Article  CAS  Google Scholar 

  7. Jung, H. H., Buesking, A. W. & Ellman, J. A. Org. Lett. 13, 3912–3915 (2011).

    Article  CAS  Google Scholar 

  8. Kolahdouzan, K. et al. ACS Catal. 10, 405–411 (2020).

    Article  CAS  Google Scholar 

  9. Lovering, F., Bikker, J. & Humblet, C. J. Med. Chem. 52, 6752–6756 (2009).

    Article  CAS  Google Scholar 

Download references

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Correspondence to Malcolm P. Huestis or Jack A. Terrett.

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Huestis, M.P., Terrett, J.A. Simple strategy towards amide bioisosteres. Nat. Chem. 14, 120–121 (2022). https://doi.org/10.1038/s41557-021-00874-0

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