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双环[1.1.1]戊烷含芳香脂氧素 A 类似物的合成与生物评价。

Synthesis and Biological Evaluation of Bicyclo[1.1.1]pentane-Containing Aromatic Lipoxin A Analogues.

机构信息

Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland.

School of Biology & Environmental Science, Diabetes Complications Research Centre, UCD Conway Institute, University College Dublin, Belfield, Dublin 4, Ireland.

出版信息

Org Lett. 2022 Aug 19;24(32):6049-6053. doi: 10.1021/acs.orglett.2c02345. Epub 2022 Aug 8.

DOI:10.1021/acs.orglett.2c02345
PMID:35938947
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9400386/
Abstract

Lipoxins are important drivers of inflammation resolution, suggesting a potential therapeutic benefit. Bicyclo[1.1.1]pentanes (BCPs) are potential isosteric replacements for arenes and/or alkyl groups within drug candidates. We carried out an asymmetric synthesis of four BCP-containing synthetic lipoxin A mimetics (BCP-sLXms) in which the key steps were a Suzuki coupling, an asymmetric ketone reduction, and a triethylborane-initiated radical bicyclopentylation. These mimetics were screened for their impact on inflammatory responses, and one imidazolo-BCP-sLXm () was found to possess high anti-inflammatory activity.

摘要

脂氧素是炎症消退的重要驱动因素，这表明它们可能具有治疗益处。双环[1.1.1]戊烷（BCPs）是药物候选物中芳烃和/或烷基的潜在等排体替代物。我们进行了含有四个 BCP 的合成脂氧素 A 类似物（BCP-sLXms）的不对称合成，其中关键步骤是铃木偶联、不对称酮还原和三乙基硼烷引发的自由基双环戊基化。这些类似物的抗炎活性进行了筛选，发现咪唑并-BCP-sLXm（）具有很高的抗炎活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b37/9400386/e063ce7f83b4/ol2c02345_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b37/9400386/8b5db59f5ba3/ol2c02345_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b37/9400386/efadd69077ab/ol2c02345_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b37/9400386/411964bcf19e/ol2c02345_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b37/9400386/559f607ccdc3/ol2c02345_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b37/9400386/dbc019597a23/ol2c02345_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b37/9400386/e063ce7f83b4/ol2c02345_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b37/9400386/8b5db59f5ba3/ol2c02345_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b37/9400386/efadd69077ab/ol2c02345_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b37/9400386/411964bcf19e/ol2c02345_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b37/9400386/559f607ccdc3/ol2c02345_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b37/9400386/dbc019597a23/ol2c02345_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b37/9400386/e063ce7f83b4/ol2c02345_0002.jpg

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