Journal
ORGANIC LETTERS
Volume 24, Issue 32, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02345
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Funding
- Irish Research Council Enterprise Partnership Scheme Ph.D. Scholarship [EPSPG/ 2019/529]
- Enterprise Partner SK Biotek Ireland
- Science Foundation Ireland Infrastructure Award [18/RI/5702]
- Irish Research Council (IRC) Government of Ireland Postdoctoral Fellowship [GOIPD/2017/1060]
- Science Foundation Ireland [11/PI/1206, 15/IA/3152]
- Science Foundation Ireland (SFI) [11/PI/1206, 15/IA/3152] Funding Source: Science Foundation Ireland (SFI)
- Irish Research Council (IRC) [GOIPD/2017/1060] Funding Source: Irish Research Council (IRC)
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The researchers synthesized BCP-containing synthetic lipoxin A4 mimetics and found that one of them exhibited high anti-inflammatory activity.
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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