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Cyclooctatetraene: A Bioactive Cubane Paradigm Complement.

Hui Xing1, Sevan D Houston1, Xuejie Chen2

  • 1School of Chemistry and Molecular Biosciences, University of Queensland (UQ), Brisbane, 4072, Queensland (QLD, Australia.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 26, 2019
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Summary
This summary is machine-generated.

Cyclooctatetraene (COT) offers a promising alternative to cubane as a phenyl ring bioisostere. This research demonstrates COT

Keywords:
agrochemicalsbioisosterecubanescyclooctatetraenespharmaceuticals

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Drug Discovery

Background:

  • Cubane has been recognized as a phenyl ring bioisostere.
  • Highly strained carbocyclic systems like cubane lack the pi character crucial for biological interactions.
  • This pi character limitation hinders cubane's utility in certain drug design scenarios.

Purpose of the Study:

  • To explore cyclooctatetraene (COT) as an alternative to cubane for overcoming electronic property restrictions.
  • To evaluate COT's performance as a phenyl ring bioisostere in pharmaceutical and agrochemical contexts.
  • To assess the complementarity between cubane and COT for discovering novel bioactive molecules.

Main Methods:

  • Utilized known pharmaceutical and agrochemical compounds as templates.
  • Synthesized and evaluated COT-containing analogs.
  • Compared the biological activity of COT analogs against cubane analogs.

Main Results:

  • Cyclooctatetraene (COT) demonstrated comparable or superior performance to cubane in multiple tested cases.
  • The study identified versatile complementarity between cubane and COT systems.
  • COT effectively addresses the lack of pi character found in cubane.

Conclusions:

  • Cyclooctatetraene (COT) is a viable and potentially advantageous alternative to cubane as a phenyl ring bioisostere.
  • The findings suggest a powerful strategy for enhanced bioactive molecule discovery by leveraging the complementary properties of COT and cubane.
  • This work expands the toolkit for medicinal chemists designing novel therapeutics and agrochemicals.