Cubane-Containing Building Blocks: the Bioisostere of Benzene Ring

In the field of drug design, cubane is considered to be the bioisostere of benzene due to its diagonal distance of the skeleton being almost the same as the diameter of benzene.¹⁾ The strategy to introduce the cubane skeleton instead of the benzene ring has gathered much interest in recent drug discovery. This is expected to improve solubility and pharmacokinetics by breaking the planarity of the entire molecule.²⁾ TCI offers a series of cubane compounds with various functional groups (1, 2, 3, 4, 5, 6) useful for derivatization, and also can provide custom synthesis of various derivatives related to these compounds.

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References

• 1) Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere
  • B. A. Chalmers, H. Xing, S. Houstin, C. Clark, S. Ghassabian, A. Kuo, B. Cao, A. Reitsma, C.-E. P. Murray, J. E. Stok, G. M. Boyle, C. J. Pierce, S. W. Littler, D. A. Winkler, P. V. Bernhardt, C. Pasay, J. J. De Voss, J. McCarthy, P. G. Parsons, G. H. Walter, M. T. Smith, H. M. Cooper, S. K. Nilsson, J. Tsanaktsidis, G. P. Savage, C. M. Williams, Angew. Chem. Int. Ed. 2016, 55, 3580.
• 2) Cubanes in Medicinal Chemistry
  • T. A. Reekie, C. M. Williams, L. M. Rendina, M. Kassiou, J. Med. Chem. 2019, 62, 1078.

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