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四氢呋喃酸片段的合成来源于万古霉素显示抑制效果金黄色葡萄球菌。

Synthesis of Tetramic Acid Fragments Derived from Vancoresmycin Showing Inhibitory Effects towards S. aureus.

机构信息

Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121, Bonn, Germany.

Institut für Pharmazeutische Mikrobiologie, Rheinische Friedrich-Wilhelms-Universität Bonn, Meckenheimer Allee 168, 53115, Bonn, Germany.

出版信息

ChemMedChem. 2020 Aug 5;15(15):1390-1393. doi: 10.1002/cmdc.202000241. Epub 2020 Jun 26.

DOI:10.1002/cmdc.202000241
PMID:32497343
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7496136/
Abstract

An efficient route to various vancoresmycin-type tetramic acids has been developed. The modular route is based on an effective Fries-type rearrangement to introduce various appending acetyl residues. The minimum inhibitory concentration (MIC) values of the new tetramic acids against Staphylococcus aureus and Escherichia coli were determined, revealing that three of the new compounds exhibit antimicrobial activity against S. aureus. These bioactive compounds were structurally most closely related to the authentic vancoresmycin building block. Additionally, the compounds induced a lial-lux bioreporter, which responds to cell wall stress induced by antibiotics that interfere with the lipid II biosynthesis cycle. These data suggest the tetramic acid moiety to be a part of the vancoresmycin pharmacophore.

摘要

已经开发出了一种将各种万古霉素型四氢酸转化为简体中文的有效方法。这种模块化的方法是基于一种有效的 Fries 型重排反应，引入了各种附加的乙酰基残基。新四氢酸对金黄色葡萄球菌和大肠杆菌的最小抑菌浓度（MIC）值进行了测定，结果表明，三种新化合物对金黄色葡萄球菌具有抗菌活性。这些生物活性化合物在结构上与万古霉素的构建块最为相似。此外，这些化合物诱导了一个 lial-lux 生物报告器，该报告器对抗生素引起的细胞壁应激作出反应，抗生素会干扰脂质 II 生物合成循环。这些数据表明四氢酸部分是万古霉素药效团的一部分。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74b/7496136/7a4eafee4864/CMDC-15-1390-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74b/7496136/ba46e5920297/CMDC-15-1390-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74b/7496136/1286bd2f33ef/CMDC-15-1390-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74b/7496136/274eb8abe2e9/CMDC-15-1390-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74b/7496136/c7da8c53d11b/CMDC-15-1390-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74b/7496136/1e55990a1958/CMDC-15-1390-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74b/7496136/7a4eafee4864/CMDC-15-1390-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74b/7496136/ba46e5920297/CMDC-15-1390-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74b/7496136/1286bd2f33ef/CMDC-15-1390-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74b/7496136/274eb8abe2e9/CMDC-15-1390-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74b/7496136/c7da8c53d11b/CMDC-15-1390-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74b/7496136/1e55990a1958/CMDC-15-1390-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b74b/7496136/7a4eafee4864/CMDC-15-1390-g002.jpg

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