Acta Poloniae Pharmaceutica, 2012, 69(6):1239-47.

Synthesis of genistein 2,3-anhydroglycoconjugates potential antiproliferative agents

Katarzyna Goj, Aleksandra Rusin, Wiesław Szeja, et al

Silesian University of Technology, Faculty of Chemistry, Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Gliwice, Poland

The title compounds, variously protected 2.3-anhydrosugars linked with genistein through an alkyl chain, were synthesized in a sequence of reactions. First step involved Ferrier rearragement of 3,4-di-O-acetyl-L-rhamnal with 3-bromopropanol to obtain 2,3-unsaturated bromoalkylglycosides. The next step was epoxidation with m-CPBA and finally these compounds were connected with genistein in reaction of 7-O-genistein tetra-butylamonium salt with 2,3-anhydro bromoalkylglycosides. Obtained glycoconjugates differ in orientation of an oxirane ring and the protecting group in a sugar moiety. All compounds were tested in vitro for antiproliferative potential in cancer cells.

波兰《波兰药物学报》，2012年11月

染料木黄酮 2,3-无水糖双共轭物潜在抗增殖试剂的合成

卡塔齐娜 下诺夫哥罗德，亚历珊德拉 卢辛，维斯劳 赛泽杰等

波兰西里西亚大学化学院有机化学、 生物有机化学和生物技术系

标题化合物，不同程度受保护的 2,3-无水糖通过烷基链与金雀异黄素连接在一起，通过一系列反应合成。第一步涉及3,4-氧-二乙烯基 -L-鼠李糖稀与3-溴丙醇的费里尔重排，获得 2，3-不饱和溴烷基糖苷。下一步是与 m-CPBA进行氧化反应，最后这些化合物通过 2，3-脱水溴烷基糖苷和7-O-金雀异黄素四丁基铵盐反应与染料木黄酮连接在一起。在糖分子中得到的糖缀合物根据环氧乙烷环的不同取向和保护性官能团有所区别。在体外测试所有化合物抑制癌细胞增殖的潜在作用。