Asymmetric total synthesis of B-ring modified (-)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus

被引：48
作者：
Anderson, JC [1 ]
Headley, C
Stapleton, PD
Taylor, PW
机构：
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[2] Univ London, Sch Pharm, Microbiol Grp, London WC1 1AX, England
来源：
TETRAHEDRON | 2005年 / 61卷 / 32期
基金：
英国医学研究理事会;
关键词：
epicatechin gallate; asymmetric synthesis; oxacillin; MRSA;
D O I：
10.1016/j.tet.2005.05.086
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two enantiomerically pure B-ring modified analogues of (-)epicatechin gallate were synthesised and their modulation of beta-lactam resistance using three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) evaluated. Sub-inhibitory concentrations (12.5 and 25 mg/L) of the two analogues fully sensitised each of the three MRSA strains to oxacillin, reducing the MIC to less than 0.5 mg/L, identical to levels achieved with ECg. Lower concentrations demonstrated that the position and degree of hydroxylation of the B-ring is important for activity. (c) 2005 Elsevier Ltd. All rights reserved.
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页码：7703 / 7711
页数：9
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