Fluoro analogs of bioactive oxy-sterols: Synthesis of an EBI2 agonist with enhanced metabolic stability
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.
Deng, Xiaohu,Sun, Siquan,Wu, Jiejun,Kuei, Chester,Joseph, Victory,Liu, Changlu,Mani, Neelakandha S.
p. 4888 - 4891
(2016/10/05)
Synthesis of 7alpha-hydroxy derivatives of regulatory oxysterols.
7alpha-Hydroxy derivatives of oxysterols are of considerable interest because of their possible involvement in regulation of cholesterol metabolism. This paper describes stereoselective syntheses and complete characterization of the 7alpha-hydroxy derivatives of four key oxysterols: 25-hydroxycholesterol, 27-hydroxycholesterol, 24(S)-hydroxycholesterol, and 24(S), 25-epoxycholesterol.
Li,Spencer
p. 529 - 535
(2007/10/03)
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