4.5 Article

Functionalized Cyclopentenones and an Oxime Ether as Antimicrobial Agents

Journal

CHEMMEDCHEM
Volume 16, Issue 18, Pages 2781-2785

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cmdc.202100369

Keywords

antimicrobial; biomass; cyclopentenones; sustainability; furfurals

Funding

  1. Fundacao para a Ciencia e a Tecnologia (FCT) [SFRH/BD/137671/2018, SFRH/BD/148211/2019, PTDC/QUI-QOR/32008/2017, UID/DTP/04138/2019, UIDB/04567/2020, UIDP/04567/2020]
  2. COMPETE Programme [SAICTPAC/0019/2015]
  3. European Union [951996]
  4. Fundação para a Ciência e a Tecnologia [SFRH/BD/148211/2019, SFRH/BD/137671/2018] Funding Source: FCT

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Naturally occurring cyclopentenones, such as palmenones and nigrosporiones, show antimicrobial activity, and derivatives accessible from biomass derivatives furfural and 5-hydroxymethylfurfural were found to exhibit significant antimicrobial activity against Gram-positive bacteria, including resistant strains like MRSA and VRE.
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 delta-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.

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