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Synthesis of Resolvin E1 and Its Conformationally Restricted Cyclopropane Congeners with Potent Anti-Inflammatory Effect

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Title: Synthesis of Resolvin E1 and Its Conformationally Restricted Cyclopropane Congeners with Potent Anti-Inflammatory Effect
Authors: Ishimura, Kohei Browse this author
Fukuda, Hayato Browse this author
Fujiwara, Koichi Browse this author →KAKEN DB
Muromoto, Ryuta Browse this author →KAKEN DB
Hirashima, Koki Browse this author
Murakami, Yuto Browse this author
Watanabe, Mizuki Browse this author →KAKEN DB
Ishihara, Jun Browse this author
Matsuda, Tadashi Browse this author →KAKEN DB
Shuto, Satoshi Browse this author →KAKEN DB
Keywords: Resolvin E1
cyclopropane congener
proresolving lipid mediator
Issue Date: 21-Jan-2021
Publisher: American Chemical Society
Journal Title: ACS medicinal chemistry letters
Volume: 12
Issue: 2
Start Page: 256
End Page: 261
Publisher DOI: 10.1021/acsmedchemlett.0c00639
Abstract: RvE1 (1) is an endogenous lipid mediator with very potent anti-inflammatory activity, which is due to the inhibition of neutrophil chemotaxis and inflammatory cytokine production and the promotion of macrophage phagocytosis. On the basis of the conformational analysis of RvE1, we designed its four cyclopropane congeners (2a-d), in which the conformationally flexible terminal C1-C4 moiety of RvE1 was rigidified by introducing stereoisomeric cyclopropanes. The four congeners and also RvE1 were efficiently synthesized via a common synthetic route. The evaluation of the anti-inflammatory effects of the compounds in mice resulted in the identification of trans-beta-CP-RvE1 (2d), which was significantly more active than RvE1, as a potential lead for antiinflammatory drugs of a novel mechanism of action.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS medicinal chemistry letters, copyright c American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Type: article (author version)
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 周東 智

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