Functionalized Cyclopentenones and an Oxime Ether as Antimicrobial Agents
Open Access
- 11 June 2021
- journal article
- research article
- Published by Wiley in ChemMedChem
- Vol. 16 (18), 2781-2785
- https://doi.org/10.1002/cmdc.202100369
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.This publication has 29 references indexed in Scilit:
- Erbium(III) Chloride in Ethyl Lactate as a Smart Ecofriendly System for Efficient and Rapid Stereoselective Synthesis of trans-4,5-Diaminocyclopent-2-enonesACS Sustainable Chemistry & Engineering, 2013
- Synthesis and Antimicrobial Activities of Oximes Derived from O‐Benzylhydroxylamine as FabH InhibitorsChemMedChem, 2012
- Stereospecific synthesis of oximes and oxime ethers of 3-azabicycles: A SAR study towards antimicrobial agentsBioorganic & Medicinal Chemistry Letters, 2010
- Reduced Vancomycin Susceptibility inStaphylococcus aureus, Including Vancomycin-Intermediate and Heterogeneous Vancomycin-Intermediate Strains: Resistance Mechanisms, Laboratory Detection, and Clinical ImplicationsClinical Microbiology Reviews, 2010
- Waves of resistance: Staphylococcus aureus in the antibiotic eraNature Reviews Microbiology, 2009
- Mild lanthanide(iii) catalyzed formation of 4,5-diaminocyclopent-2-enones from 2-furaldehyde and secondary amines: a domino condensation/ring-opening/electrocyclization processChemical Communications, 2007
- Emergence and resurgence of meticillin-resistant Staphylococcus aureus as a public-health threatThe Lancet, 2006
- Molecular Properties That Influence the Oral Bioavailability of Drug CandidatesJournal of Medicinal Chemistry, 2002
- Novel Fluoroquinolone Antibacterial Agents Containing Oxime-Substituted (Aminomethyl)pyrrolidines: Synthesis and Antibacterial Activity of 7-(4-(Aminomethyl)-3-(methoxyimino)pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro- 4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic Acid (LB20304),1Journal of Medicinal Chemistry, 1997
- Methicillin-resistant staphylococciJournal of Clinical Pathology, 1961