Asymmetric synthesis and biological evaluation of 1,3- and 1,4-disubstituted benzo-type lipoxin A4 analogues |
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| Authors: | Gavin G. Haberlin Ciara McCarthy Robert Doran Christine E. Loscher Patrick J. Guiry |
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| Affiliation: | 1. Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland;2. School of Biotechnology, Dublin City University, Dublin 9, Ireland |
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| Abstract: | The asymmetric synthesis of 1,3 and 1,4-disubstituted aromatic lipoxin A4 analogues has been accomplished. A total of eight analogues were synthesised in a convergent approach utilising Sharpless asymmetric epoxidation, asymmetric reduction and intermolecular Heck reactions. The set of analogues were assessed for their effect on the production of cytokines IL-12p40, IL-23, IL-6, IL-1β and TNFα. A positive inhibitory result was observed for the production of IL-6 and IL-1β. |
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| Keywords: | Lipoxins Asymmetric synthesis Analogues Inflammation Eicosanoids |
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