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

H. Fukuda,Kotaro Matsubara,Ayaka Hamaguchi,Hina Nishikoori,Mayu Shinohara,Jun Takouda,Kohsuke Takeda,Keijo Fukushima,Keita Komine,Koichi Fujiwara,Mizuki Watanabe,Jun Ishihara,Hiromichi Fujino,Satoshi Shuto

Published 2025 in Journal of Organic Chemistry

ABSTRACT

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.

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