Asymmetric synthesis and biological evaluation of 1,3- and 1,4-disubstituted benzo-type lipoxin A4 analogues

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 wer...

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Published inTetrahedron Vol. 70; no. 38; pp. 6859 - 6869
Main Authors Haberlin, Gavin G., McCarthy, Ciara, Doran, Robert, Loscher, Christine E., Guiry, Patrick J.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 23.09.2014
Subjects
Analogues
Asymmetric synthesis
Eicosanoids
Inflammation
Lipoxins
Lipoxins
Eicosanoids
Inflammation
Asymmetric synthesis
Analogues
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.07.029