Synthesis and antibacterial activity of hydrolytically stable (−)-epicatechin gallate analogues for the modulation of β-lactam resistance in Staphylococcus aureus

Bioorganic & Medicinal Chemistry Letters
2005.0

Abstract

Hydrolytically more stable analogues of (-)-epicatechin gallate (ECg) have been synthesised from ECg where an amine or amide function has been substituted for the ester linkage that joins the C-ring with the galloyl D-ring. Sub-inhibitory concentrations (25 mg/L) of the amide analogue 7, possessing the natural C-3 stereochemistry, were able to reduce the resistance to oxacillin of three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) comparable to levels achieved with ECg.

Knowledge Graph

Similar Paper

Synthesis and antibacterial activity of hydrolytically stable (−)-epicatechin gallate analogues for the modulation of β-lactam resistance in Staphylococcus aureus
Bioorganic & Medicinal Chemistry Letters 2005.0
Anti-staphylococcal activity and β-lactam resistance attenuating capacity of structural analogues of (−)-epicatechin gallate
Bioorganic & Medicinal Chemistry Letters 2011.0
Synthesis and antimicrobial activities of 3-O-alkyl analogues of (+)-catechin: Improvement of stability and proposed action mechanism
European Journal of Medicinal Chemistry 2010.0
Anti-MRSA activity of alkyl gallates
Bioorganic & Medicinal Chemistry Letters 2002.0
Synthesis and evaluation of stereoisomers of methylated catechin and epigallocatechin derivatives on modulating P-glycoprotein-mediated multidrug resistance in cancers
European Journal of Medicinal Chemistry 2021.0
Solid-phase synthesis and antibacterial activity of hydroxycinnamic acid amides and analogues against methicillin-resistant Staphylococcus aureus and vancomycin-resistant S. aureus
Bioorganic & Medicinal Chemistry Letters 2006.0
Green tea catechins as a BACE1 (β-Secretase) inhibitor
Bioorganic & Medicinal Chemistry Letters 2003.0
O-Methylglucogalloyl esters: Synthesis and evaluation of their antimycotic activity
Bioorganic & Medicinal Chemistry Letters 2005.0
Synthesis and Preliminary Anticancer Activity Studies of C4 and C8-Modified Derivatives of Catechin Gallate (CG) and Epicatechin Gallate (ECG)
The Journal of Organic Chemistry 2006.0
18β-Glycyrrhetinic Acid Derivatives Possessing a Trihydroxylated A Ring Are Potent Gram-Positive Antibacterial Agents
Journal of Natural Products 2016.0