合成吡咯烷融合的β-内酰胺作为潜在的β-内酰胺酶抑制剂

IF 2.8 4区 化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2024-08-28 DOI:10.1002/ajoc.202400364
Sari Deketelaere, Carlos Diez-Poza, Margot Aelbrecht, Jonas Mortier, Bram Van Den Bossche, Jorick Franceus, Tom Desmet, Kristof Van Hecke, Chris Stevens, Matthias D'hooghe
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引用次数: 0

摘要

本研究开发了一种用于制备新型 3,4-吡咯烷融合 β-内酰胺的合成方案。在关键反应步骤中,通过氨基基团诱导、叔丁醇钾促进的 3-酰氨基-4-环氧乙烷基-β-内酰胺的分子内环闭合,构建了拟议的 2,6-二氮杂双环[3.2.0]庚烷-7-酮支架。另外,还可以通过三酸钪介导的催化方法实现所需的环化。通过这种方法,合成了一组立体定义的 3,4-吡咯烷融合的 β-内酰胺,并将其作为 β-内酰胺酶抑制剂进行了初步评估。通过这些一线生物评估,确定了一种 2-苯甲酰基-6-(4-甲氧基苯基)取代的二氮杂双环结构,可作为进一步优化 β-内酰胺酶抑制剂研究的起点。
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Synthesis of pyrrolidine-fused β-lactams as potential β-lactamase inhibitors
A synthetic protocol for the preparation of novel 3,4-pyrrolidine-fused β-lactams was developed. The proposed 2,6-diazabicyclo[3.2.0]heptan-7-one scaffolds were constructed through an amido group-induced, potassium tert-butoxide-promoted intramolecular ring closure of 3-acylamino-4-oxiranyl-β-lactams as the key reaction step. Alternatively, the desired cyclization was also effected by means of a scandium triflate-mediated catalytic approach. In this way, a set of stereodefined 3,4-pyrrolidine-fused β-lactams was synthesized, which were preliminary evaluated as β-lactamase inhibitors. These first-line biological assessments led to the identification of a 2-benzoyl-6-(4-methoxyphenyl)-substituted diazabicyclo structure as an eligible starting point for further β-lactamase inhibitor optimization studies.
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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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