Design and synthesis of novel prostaglandin E-2 ethanolamide and glycerol ester probes for the putative prostamide receptor(s)

作者：Shelnut Erin L; Nikas Spyros P; Finnegan David F; Chiang Nan; Serhan Charles N; Makriyannis Alexandros^*

来源：Tetrahedron Letters, 2015, 56(11): 1411-1415.

DOI：10.1016/j.tetlet.2015.01.164

• Endocannabinoids
• Prostamides
• Prostaglandin glycerol ester
• Lipids

Novel prostaglandin-ethanolamide (PGE(2)-EA) and glycerol ester (2-PGE(2)-G) analogs were designed and synthesized to aid in the characterization of a putative prostamide receptor. Our design incorporates the electrophilic isothiocyanato and the photoactivatable azido groups at the terminal tail position of the prototype. Stereoselective Wittig and Horner-Wadsworth-Emmons reactions install the head and the tail moieties of the PGE(2) skeleton. The synthesis is completed using Mitsunobu azidation and peptide coupling as the key steps. A chemoenzymatic synthesis for the 2-PGE(2)-G is described for first time.

• 出版日期2015-3-11
• 单位河北医科大学; 东北大学