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Volumn 15, Issue 10, 2005, Pages 2633-2635

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

Author keywords

( ) Epicatechingallate analogues; MRSA; Lactam antibiotics

Indexed keywords

BETA LACTAM ANTIBIOTIC; EPICATECHIN GALLATE; FLAVONOID; METICILLIN; OXACILLIN;

EID: 18144400595     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.03.063     Document Type: Article
Times cited : (30)

References (19)
  • 4
    • 33846504339 scopus 로고    scopus 로고
    • C.F. Ambile-Cuevas Horizon Scientific Wymondham
    • N. Firth C.F. Ambile-Cuevas Multiple Drug Resistant Bacteria 2003 Horizon Scientific Wymondham 33 60
    • (2003) Multiple Drug Resistant Bacteria , pp. 33-60
    • Firth, N.1
  • 8
    • 0037538675 scopus 로고    scopus 로고
    • 1H NMR signal of C-2H (δ 4.90, s) compares favourably with the analogous signal in 5,7,3′,4′-tetra-O-benzyl-(-) -epicatechin (δ 4.91, s) and is in stark contrast to the same signal in 5,7,3′,4′-tetra-O-benzyl-(+)-catechin (δ 4.63, d, J = 8.5 Hz) in W. Tuckmantel, A.P. Kozikowski, and L.J. Romanczyk J. Am. Chem. Soc. 121 1999 12073
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 12073
    • Tuckmantel, W.1    Kozikowski, A.P.2    Romanczyk, L.J.3
  • 13
    • 85030798164 scopus 로고    scopus 로고
    • note
    • 2O, EtOH, rt, 14 h, in 60% yield over two-steps
  • 14
    • 85030802561 scopus 로고    scopus 로고
    • note
    • The natural C-3 stereochemistry (R) was confirmed based on the small coupling constant for the C-2H (δ 5.11, d, J = 2.6 Hz) indicating the relative cis-stereochemistry between C-2 and C-3 as before (Ref. 8)
  • 17
    • 85030803857 scopus 로고    scopus 로고
    • note
    • These were assigned based on the coupling constants their C-2H protons as before (Ref. 8), 10 (natural 3R stereochemistry) C-2H (δ 5.09, d, J = 2.2 Hz) and 11 (3S) C-2H (δ 4.70, m, J = 7.6 Hz)
  • 18
    • 85030804172 scopus 로고    scopus 로고
    • note
    • 2Cl in the presence of 2-methyl-2-butene in t-BuOH and pH 4 buffer in 58% yield over two-steps
  • 19
    • 85030793699 scopus 로고    scopus 로고
    • note
    • 4 colony-forming units (cfu) in 100 μL of Mueller-Hinton broth (Oxoid, Basingstoke, UK) supplemented with 2% w/v NaCl. Doubling dilutions of oxacillin were employed. MIC values were recorded after incubation of the trays at 35°C for 24 h; S. aureus ATCC29213 was used as the standard. The intrinsic anti-staphylococcal activity of compounds was also evaluated using these methods


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