Heteroaromatic Lipoxin A4 Analogues

This review of the chemistry and biology of stable lipoxin analogues describes for the first time the synthesis of an enantiomerically pure form of pyridine-containing LXA4, as well as a route to synthesizing a thiophene-containing LXA4 analogue.

In this thesis Colm Duffy reviews the chemistry and biology of stable lipoxin analogues. Colm has prepared for the first time ever a pyridine-containing LXA4 analogue in enantiomerically pure form. Biological evaluation determined that both epimers at the benzylic position suppress key cytokines known to be involved in inflammatory disease, with the (R)-epimer proving most efficacious. Moreover the author developed an excellent route to a related thiophene-containing analogue that also showed interesting biological activity. Both routes have inspired further work in the synthesis of further heteroaromatic analogues for biological evaluation.

Nominated by University College Dublin as an outstanding PhD thesis Author describes for the first time the synthesis of an enantiomerically pure form of pyridine-containing LXA4 Description of an excellent route to a thiophene-containing LXA4 analogue Includes supplementary material: sn.pub/extras

Inhalt
Introduction.- Recent advances in the chemistry and biology of stable synthetic Lipoxin analogues.- Synthesis of Heck coupling partner for the preparation of heteroaromatic Lipoxin A4 analogues.- Synthesis and biological evaluation of pyridine-containing Lipoxin A4 analogues.- Thiophene-containing Lipoxin A4 analogues: synthesis and their effect on the production of key cytokines.- Towards the synthesis of various heteroaromatic Lipoxin A4 analogues.