合成带有叠氮化物标记的 2,3-二氢-4-喹诺酮文库。
Synthesis of an azide-tagged library of 2,3-dihydro-4-quinolones.
机构信息
Department of Chemistry, University of Chicago, 5735 S. Ellis Ave., Chicago, Illinois 60637, USA.
出版信息
J Org Chem. 2010 Mar 5;75(5):1756-9. doi: 10.1021/jo9025447.
Abstract
We describe the assembly of a 960-member library of tricyclic 2,3-dihydro-4-quinolones using a combination of solution-phase high-throughput organic synthesis and parallel chromatographic purification. The library was produced with high efficiency and complete chemo- and diastereoselectivity by diversification of an azide-bearing quinolone via a sequence of [4 + 2] cycloadditions, N-acylations, and reductive aminations. The azide-functionalization of this library is designed to facilitate subsequent preparation of fluorescent or affinity probes, as well as small-molecule/surface conjugation.
摘要
我们描述了使用溶液相高通量有机合成和并行色谱纯化相结合的方法来组装 960 个成员的三环 2,3-二氢-4-喹诺酮文库。通过一系列[4 + 2]环加成、N-酰化和还原胺化反应，对带有叠氮化物的喹诺酮进行多样化，以高效率和完全的化学和立体选择性合成了该文库。该文库的叠氮功能化旨在方便随后制备荧光或亲和探针以及小分子/表面缀合。
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