化学
酮
戊烷
双环分子
全合成
立体化学
烷基
组合化学
有机化学
作者
Benjamin C. Owen,Monica de Gaetano,Andrew Gaffney,Catherine Godson,Patrick J. Guiry
出处
期刊:Organic Letters
[American Chemical Society]
日期:2022-08-08
卷期号:24 (32): 6049-6053
被引量:8
标识
DOI:10.1021/acs.orglett.2c02345
摘要
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 A4 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 (6a) was found to possess high anti-inflammatory activity.
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