Cyclooctatetraene: A Bioactive Cubane Paradigm Complement

Hui Xing, Sevan D. Houston, Xuejie Chen, Sussan Ghassabian, Tyler Fahrenhorst-Jones, Andy Kuo, Cody Ellen P. Murray, Kyna-Anne Conn, Kara N. Jaeschke, Da Yun Jin, Cielo Pasay, Paul V. Bernhardt, Jed M. Burns, John Tsanaktsidis, G. Paul Savage, Glen M. Boyle, James J. De Voss, James McCarthy, Gimme H. Walter, Thomas H.J. BurneMaree T. Smith, Jian Ke Tie, Craig M. Williams

Research output: Contribution to journalArticleResearchpeer-review

25 Citations (Scopus)

Abstract

Cubane was recently validated as a phenyl ring (bio)isostere, but highly strained caged carbocyclic systems lack π character, which is often critical for mediating key biological interactions. This electronic property restriction associated with cubane has been addressed herein with cyclooctatetraene (COT), using known pharmaceutical and agrochemical compounds as templates. COT either outperformed or matched cubane in multiple cases suggesting that versatile complementarity exists between the two systems for enhanced bioactive molecule discovery.

Original languageEnglish
Pages (from-to)2729-2734
Number of pages6
JournalChemistry - A European Journal
Volume25
Issue number11
DOIs
Publication statusPublished - 21 Feb 2019
Externally publishedYes

Keywords

  • agrochemicals
  • bioisostere
  • cubanes
  • cyclooctatetraenes
  • pharmaceuticals

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