Design and Synthesis of Cyclopropane Congeners of Resolvin E2 with Azidopropoxy Chain toward a Chemical Tool for Probing the Anti-inflammatory Activity.

Resolvins (Rvs), unsaturated fatty acid metabolites are a new type of anti-inflammatory lipid mediator that promotes inflammation resolution, so that these compounds can be efficient leads for developing new anti-inflammatory drugs. We have previously developed a cyclopropane (CP) congener of resolving E2 (RvE2), i.e., CP-RvE2, as a stable equivalent of RvE2. In this study, based on the stable equivalent of CP-RvE2, we designed and synthesized AP-β-CP-RvE2, in which an azidopropoxy (AP) group was introduced into the 5-, 18-, or 20-position of CP-RvE2, as potential chemical probes. We found that among them, 5-AP-β-CP-RvE2 had anti-inflammatory activity same as RvE2, suggesting its potential utility as a chemical probe.