Design and synthesis of novel prostaglandin E2 ethanolamide and glycerol ester probes for the putative prostamide receptor(s)

TETRAHEDRON LETTERS

卷:56

Article

Shelnut, Erin L.^1,2,3  Nikas, Spyros P.^1,2,3  Finnegan, David F.^1,2,3  Chiang, Nan^4,5  Serhan, Charles N.^4,5  Makriyannis, Alexandros^1,2,3,6 

[1] Northeastern Univ, Ctr Drug Discovery, Boston, MA 02115 USA

[2] Northeastern Univ, Dept Chem & Chem Biol, Boston, MA 02115 USA

[3] Northeastern Univ, Dept Pharmaceut Sci, Boston, MA 02115 USA

[4] Brigham & Womens Hosp, Harvard Inst Med, Dept Anesthesiol Perioperat & Pain Med, Ctr Expt Therapeut & Repeifus Injuiy, Boston, MA 02115 USA

[5] Harvard Univ, Sch Med, Boston, MA 02115 USA

[6] King Abdulaziz Univ, Jeddah 22254, Saudi Arabia

关键词: Endocannabinoids;    Prostamides;    Prostaglandin glycerol ester;    Lipids;   

DOI  :  10.1016/j.tetlet.2015.01.164

来源: Elsevier

【 摘 要 】

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. (C) 2015 Published by Elsevier Ltd.

【 授权许可】

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