Rajput Vishal Kumar, Leffler Hakon, Nilsson Ulf J, Mukhopadhyay Balaram
Centre for Analysis and Synthesis, Department of Chemistry, Lund University, POB 124, SE-221 00 Lund, Sweden; Indian Institute of Science Education and ResearchKolkata, Mohanpur, Nadia 741252, India.
Section MIG, Department of Laboratory Medicine, Lund University, Sölvegatan 23, SE-223 62 Lund, Sweden.
Bioorg Med Chem Lett. 2014 Aug 1;24(15):3516-20. doi: 10.1016/j.bmcl.2014.05.063. Epub 2014 Jun 9.
A collection of iminocoumarylmethyl glycoside derivatives have been prepared by copper-catalyzed multi-component reaction of carbohydrate propargyl derivatives, sulfonyl azides, and salicylaldehyde or o-hydroxy acetophenone. The method is simple, versatile to all three components, and exceptionally high yielding. The carbohydrate N-sulfonyl iminocoumarine hybrid molecules were evaluated for binding galectin-1, -2, -3, -4N, -4C, -7, -8N, -9N, and 9C using a competitive fluorescence polarization assay. Selective compounds were identified against galectin-3, 7, 8N, and 9N with up to 40-fold affinity enhancements relative to methyl α-d-galactopyranoside due to the coumarylmethyl moieties.
通过碳水化合物炔丙基衍生物、磺酰叠氮化物与水杨醛或邻羟基苯乙酮的铜催化多组分反应，制备了一系列亚氨基香豆素甲基糖苷衍生物。该方法简单，对所有三种组分都具有通用性，且产率极高。使用竞争性荧光偏振测定法评估了碳水化合物N-磺酰基亚氨基香豆素杂合分子与半乳糖凝集素-1、-2、-3、-4N、-4C、-7、-8N、-9N和9C的结合情况。由于香豆素甲基部分，鉴定出了对半乳糖凝集素-3、7、8N和9N具有选择性的化合物，其亲和力相对于α-d-吡喃半乳糖苷甲基酯提高了40倍。
