Fluorous mixture synthesis of two libraries with hydantoin-, and benzodiazepinedione-fused heterocyclic scaffolds.
Fluorous mixture synthesis of two libraries with hydantoin-, and benzodiazepinedione-fused heterocyclic scaffolds.
复制标题
两个具有乙内酰脲和苯二氮卓酮稠合杂环支架的文库的氟混合物合成。
DOI：
10.1021/cc060061e
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发表时间：
2006
影响因子：
--
通讯作者：
Kassel,DanielB
中科院分区：
文献类型：
--
作者：
Zhang,Wei;Lu,Yimin;Hiu-TungChen,Christine;Zeng,Lu;Kassel,DanielB
面向多样性的合成(DOS)和氟混合物合成(FMS)是组合化学的两个方面。DOS生成具有骨架、取代和立体化学变化的文库支架，而FMS是一种高效的文库生产工具。本文将这两个方面结合起来应用于两个新型杂环化合物库的固相合成。不同含氟氨基酸的混合物经过[3+2]环加成反应，然后进行后缩合反应。然后用含氟高效液相色谱分离混合物。通过环化去除氟标记，以提供作为单独的、纯的和结构定义的分子的海因和苯二氮杂二酮稠合杂环化合物。应用MS-DILC纯化和并行四通道LC/MS分析进一步提高了FMS的效率。
Diversity-oriented synthesis (DOS) and fluorous mixture synthesis (FMS) are two aspects of combinatorial chemistry. DOS generates library scaffolds with skeletal, substitution, and stereochemistry variations, whereas FMS is a highly efficient tool for library production. The combination of these two aspects in solution-phase synthesis of two novel heterocyclic compound libraries is presented in this paper. Mixtures of different fluorous amino acids undergo [3 + 2] cycloadditions followed by postcondensation reactions. The mixtures are then demixed by fluorous HPLC. Fluorous tags are removed by cyclization to afford hydantoin- and benzodiazepinedione-fused heterocyclic compounds as individual, pure, and structurally defined molecules. The application of MS-directed HPLC purification and parallel four-channel LC/MS analysis further increases the efficiency of FMS.