Fluoro analogs of bioactive oxy-sterols: Synthesis of an EBI2 agonist with enhanced metabolic stability

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• 作者：Xiaohu Deng ; Siquan Sun ; Jiejun Wu ; Chester Kuei ; Victory Joseph ; Changlu Liu ; Neelakandha S. Mani ; ^{nmani@its.jnj.com" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Oxysterols ; Fluoro oxysterol ; Immune response ; Epstein&ndash ; Barr virus ; GPR 183 ; EBI2 agonist
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2016
• 出版时间：15 October 2016
• 年：2016
• 卷：26
• 期：20
• 页码：4888-4891
• 全文大小：834 K

文摘

Synthesis of several 7-hydroxy oxysterols and their potential roles as signaling molecules in the innate and adaptive immune responses is discussed. Discovery of a new, fluorinated, synthetic analog of the 7α,25-dihydroxycholesterol—the endogenous ligand of GPR 183 (EBI2), a G-protein coupled receptor highly expressed upon Epstein–Barr virus infection is described. Fluoro oxysterol 12 showed good metabolic stability while maintaining excellent EBI2 agonist activity.