Synthesis of the methyl ester of 17(R/ S)-Me-RvD5n-3 DPA and relief of postoperative pain in male mice

Org Biomol Chem. 2024 Dec 4;22(47):9266-9270. doi: 10.1039/d4ob01534g.

Abstract

The synthesis and biological evaluation of 17(R/S)-Me-RvD5n-3 DPA, an analog of the specialized pro-resolving mediators RvD5 and RvD5n-3 DPA, are presented. The synthesis was successfully accomplished utilizing Midland Alpine borane reduction, Sonogashira cross-coupling and a one-pot hydrozirconation/iodination protocol. In vivo evaluation of RvD5, RvD5n-3 DPA and 17(R/S)-Me-RvD5n-3 DPA in a mouse model of fracture revealed that all three compounds inhibited postoperative pain in male mice, but not in female mice.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Esters / chemical synthesis
  • Esters / chemistry
  • Esters / pharmacology
  • Female
  • Male
  • Mice
  • Molecular Structure
  • Pain, Postoperative* / drug therapy

Substances

  • Esters