Synthesis and biological evaluation of optically active conjugated γ- and δ-lactone derivatives

Bioorg Med Chem Lett. 2012 Sep 15;22(18):5814-8. doi: 10.1016/j.bmcl.2012.07.090. Epub 2012 Aug 2.

Abstract

An efficient synthesis of racemic and both enantiomeric forms of heteroaryl substituted γ- and δ-lactone derivatives derived from allyl and homoallyl alcohol backbones has been accomplished via ring closing metathesis reaction. 2-Heteroaryl substituted allyl and homoallyl alcohols have been efficiently resolved through enzymatic method with high ee (97-99%) and known stereochemistry. Antimicrobial and antioxidant activities of target lactones were evaluated.

Publication types

  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Bacteria / drug effects*
  • Dose-Response Relationship, Drug
  • Fungi / drug effects*
  • Lactones / chemical synthesis
  • Lactones / chemistry
  • Lactones / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Alcohols
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Antioxidants
  • Lactones