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.

引用

页码：7703 / 7711

页数：9

共 51 条

[1]

Ahmad N, 1999, NUTR REV, V57, P78, DOI 10.1111/j.1753-4887.1999.tb06927.x

[2]

ALEXANDRE C, 1971, B SOC CHIM FR, P1837

[3]

Amarowicz R, 2000, NAHRUNG, V44, P60, DOI [10.1002/(SICI)1521-3803(20000101)44:1&lt

[4]

60::AID-FOOD60&gt

[5]

3.0.CO

[6]

2-L, 10.1002/(SICI)1521-3803(20000101)44:1<60::AID-FOOD60>3.3.CO

[7]

2-C]

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

Anderson, JC ;

Headley, C ;

Stapleton, PD ;

Taylor, PW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (10) :2633-2635

[9] Investigation of the asymmetric ionic Diels-Alder reaction for the synthesis of cis-decalins [J].

Anderson, JC ;

Blake, AJ ;

Graham, JP ;

Wilson, C .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (16) :2877-2885

[10]

Aramini A, 2000, EUR J ORG CHEM, V2000, P1793

← 1 2 3 4 5 6 →