2024-03-29T14:39:31Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/832042022-11-17T02:08:08Zhdl_2115_20044hdl_2115_124Synthesis of Resolvin E3, a Proresolving Lipid Mediator, and Its Deoxy Derivatives : Identification of 18-Deoxy-resolvin E3 as a Potent Anti-Inflammatory AgentFukuda, HayatoIkeda, Hiroyuki1000030455597Muromoto, RyutaHirashima, KokiIshimura, Kohei1000040837853Fujiwara, KoichiAoki-Saito, HarukaHisada, Takeshi1000020507173Watanabe, MizukiIshihara, Jun1000020212219Matsuda, Tadashi1000070241346Shuto, Satoshiopen accessThis document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in Journal of organic chemistry, copyright c American Chemical Society after peer review. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.joc.0c01701.460We synthesized RvE3 and its deoxy derivatives, 17-deoxy-RvE3 and 18-deoxy-RvE3, by a common route via Sonogashira coupling as a key step. The evaluation of their anti-inflammatory activities revealed that 18-deoxy-RvE3 was remarkably more potent than the parent RvE3 and significantly active at a 300 fg dose in mice; additionally, 17-deoxy-RvE3 was significantly less potent than the parent RvE3. For the first time, we found that the 17-hydroxy group of RvE3 is very important for anti-inflammatory activity.American Chemical Society2020-11-06engjournal articleAMhttp://hdl.handle.net/2115/83204https://doi.org/10.1021/acs.joc.0c017010022-3263Journal of organic chemistry85211419014200https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/83204/1/WoS_96846_Shuto.pdfapplication/pdf873.07 KB2020-11-06