Synthesis and anti-tumor activities of methyl 2-O-aryl-6-O-aryl′-d-glucopyranosides
作者:Hefang Shi、Bingcheng Zhou、Wenwen Li、Zhimin Shi、Biao Yu、Renxiao Wang
DOI:10.1016/j.bmcl.2010.03.045
日期:2010.5
A synthetic method of introducing bulky aryl groups at the 2-O- and 6-O-positions on glucopyranosides was developed. A total of 37 new compounds of this class were obtained successfully. These compounds were tested on several tumor cell lines by MTT assays, and some of them exhibited encouraging inhibitory activities. The most potent compound, CAB-SHZH-27, exhibited EC50 values of 14, 12, and 10 μmol/L
提出了在吡喃葡萄糖苷的2- O-和6- O-位引入大体积芳基的合成方法。总共成功获得了37种此类新化合物。通过MTT测定法在多种肿瘤细胞系上测试了这些化合物,其中一些表现出令人鼓舞的抑制活性。最有效的化合物CAB-SHZH- 27在A549,MDA-MB-231和HeLa细胞上的EC 50值分别为14、12和10μmol/ L。初步的结构-活性关系分析表明,d-葡萄糖核心上的两个游离羟基对于此类化合物的生物活性是必不可少的,而6- O上的芳基则必不可少-位置比2- O位置的影响更明显。在我们的MTT分析中还观察到了此类化合物有趣的“开-关”机制,这仍有待探索。