Bioorganic & medicinal chemistry letters

Aromatic farnesyl diphosphate analogues: vinyl triflate-mediated synthesis and preliminary enzymatic evaluation

C Zhou, Y Shao, RA Gibbs

文献索引：Zhou, Chunmei; Shao, Ying; Gibbs, Richard A. Bioorganic and Medicinal Chemistry Letters, 2002 , vol. 12, # 10 p. 1417 - 1420

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被引用次数: 17

摘要

A stereocontrolled vinyl triflate-based synthetic route has been used to prepare four analogues of farnesyl diphosphate (FPP) where the terminal isoprene units have been replaced with aromatic moieties. Two of these analogues exhibit no productive interaction with protein farnesyltransferase, but the 2-naphthyl derivative 2 is a modest inhibitor of the enzyme, and the para-biphenyl derivative 4 is a surprisingly effective alternative substrate.