Functionalized Cyclopentenones and an Oxime Ether as Antimicrobial Agents

ChemMedChem. 2021 Sep 16;16(18):2781-2785. doi: 10.1002/cmdc.202100369. Epub 2021 Jul 2.

Abstract

Several naturally occurring cyclopentenones, such as palmenones and nigrosporiones, exhibit antimicrobial activity. Herein we describe the antimicrobial activity of cyclopentenones and derivatives that can be easily accessed from biomass derivatives furfural and 5-hydroxymethylfurfural. Upon screening a range of functionalized trans-diamino-cyclopentenones (DCPs) and δ-lactone-fused cyclopentenones (LCPs), an oxime ether derivative of DCP was identified that exhibited remarkable antimicrobial activity against Gram-positive bacteria, including resistant strains such as methicillin-resistant S. aureus (MRSA) and vancomycin-resistant E. faecalis (VRE) strains.

Keywords: antimicrobial; biomass; cyclopentenones; furfurals; sustainability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Cyclopentanes / chemical synthesis
  • Cyclopentanes / chemistry
  • Cyclopentanes / pharmacology*
  • Dose-Response Relationship, Drug
  • Enterococcus faecalis / drug effects*
  • Ether / chemical synthesis
  • Ether / chemistry
  • Ether / pharmacology*
  • Methicillin-Resistant Staphylococcus aureus / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Oximes / chemical synthesis
  • Oximes / chemistry
  • Oximes / pharmacology*
  • Structure-Activity Relationship
  • Vancomycin Resistance / drug effects

Substances

  • Anti-Bacterial Agents
  • Cyclopentanes
  • Oximes
  • Ether
  • cyclopentenone