螺环丙基吡咯烷类作为新型α-L-岩藻糖苷酶抑制剂系列
Spirocyclopropyl pyrrolidines as a new series of alpha-L-fucosidase inhibitors.
作者信息
Laroche Christophe, Behr Jean-Bernard, Szymoniak Jan, Bertus Philippe, Schütz Catherine, Vogel Pierre, Plantier-Royon Richard
机构信息
Laboratoire Réactions Sélectives et Applications, Université de Reims Champagne-Ardenne, UMR URCA/CNRS 6519, UFR Sciences, BP 1039, F-51687 Reims Cedex 2, France.
出版信息
Bioorg Med Chem. 2006 Jun 15;14(12):4047-54. doi: 10.1016/j.bmc.2006.02.005. Epub 2006 Feb 20.
Polyhydroxy 4-azaspiro[2.4]heptane derivatives (spirocyclopropyl iminosugars) were prepared in four to six steps from readily available protected aldoses. The key step of the reaction sequence involves a titanium-mediated aminocyclopropanation of glycononitriles with subsequent cyclization. Five new polyhydroxypyrrolidines so-obtained have been evaluated for their ability to inhibit 16 glycosidases. One of them exhibits selective inhibition of alpha-L-fucosidase from bovine kidney (Ki=1.6 microM, competitive).
多羟基4-氮杂螺[2.4]庚烷衍生物（螺环丙基亚氨基糖）由易得的保护醛糖经四至六步反应制备而成。该反应序列的关键步骤涉及钛介导的糖腈的氨基环丙烷化反应及后续环化反应。对由此得到的5种新的多羟基吡咯烷抑制16种糖苷酶的能力进行了评估。其中一种对牛肾来源的α-L-岩藻糖苷酶表现出选择性抑制作用（Ki = 1.6 μM，竞争性抑制）。
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