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 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.