Efficient Synthesis of New 2-Cycloalk(en)ylpropanoic Acid Derivatives—Medium and Large Rings as Bioisosteres of Alkylphenyl Moieties?


  • This work was supported by the Fonds der Chemischen Industrie and the Bundesministerium für Forschung und Technologie. We thank Hüls AG (Marl) and Firmenich S. A. (Genf) for financial and material support.

  • Dedicated to Professor Gunther Seitz on the occasion of his 60th birthday


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COX and LOX inhibitors analogous to 2-arylpropanoic acids have been synthesized (general route is shown below) and can be viewed as mimetics of arachidonic acid. Remarkably, even medium-sized cycloalkanones reacted almost quantitatively with zinc cuprates. Interesting differences in pharmacological activities related to ring size were observed.