The dirhodium tetraacetate-catalyzed iminoiodane-mediated reaction of 1,3-dimethyl-5-vinyluracil with phenyl sulfamate provided a high yield of 5-(1-acetyl-2-phenylsulfamoyl)ethyluracil via regioselective nucleophilic ring opening by acetate anion of the transiently formed 5-(1,2)-N-phenylsulfonylaziridine intermediate. This 1,2-oxyamidation reaction was found to be general for a variety of aryl- and alkylsulfamates as well as for various 1,3-dialkyl-5-vinyluracil derivatives. Addition of an alcohol to the reaction mixture allowed formation of the corresponding 1-alkoxy products. A selection of the substituted uracil derivatives prepared by this procedure was evaluated for cytotoxic activities in HCT-116 and HepG2 cancer cell lines and showed either no or modest activities. Further evaluation for α-glucosidase inhibition revealed that compounds 15ca and 15da were more active than acarbose, the reference inhibitor. This methodology thus allows efficient preparation of highly functionalized uracil derivatives thereby providing a synthetic route to novel compounds with potentially useful biological activities.

中文翻译：

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使用芳基和烷基氨基磺酸盐的 5-乙烯基尿嘧啶衍生物的铑催化亚氨基碘烷介导的酰胺化研究。

四乙酸二铑催化的亚氨基碘烷介导的 1,3-二甲基-5-乙烯基尿嘧啶与氨基磺酸苯酯的反应通过瞬时乙酸根阴离子的区域选择性亲核开环提供了高产率的 5-(1-乙酰基-2-苯基氨磺酰基)乙基尿嘧啶。形成 5-(1,2)- N-苯基磺酰基氮丙啶中间体。发现这种 1,2-氧酰胺化反应对于各种芳基氨基磺酸盐和烷基氨基磺酸盐以及各种 1,3-二烷基-5-乙烯基尿嘧啶衍生物是通用的。向反应混合物中加入醇允许形成相应的1-烷氧基产物。在 HCT-116 和 HepG2 癌细胞系中评估了选择的通过该程序制备的取代尿嘧啶衍生物的细胞毒活性，并显示无活性或适度活性。对 α-葡萄糖苷酶抑制的进一步评估表明，化合物15ca和15da比参考抑制剂阿卡波糖更具活性。因此，该方法允许高效制备高度官能化的尿嘧啶衍生物，从而为具有潜在有用生物活性的新型化合物提供合成途径。