An Efficient Synthesis of 3-Substituted <i>N</i>-Glycoside Indoles Useful as Sodium-Dependent Glucose Transporter Inhibitors
作者:Xun Li、Kenneth M. Wells、Shawn Branum、Sandra Damon、Scott Youells、Derek A. Beauchamp、David Palmer、Stephen Stefanick、Ronald K. Russell、William Murray
DOI:10.1021/op3001355
日期:2012.11.16
A practical synthesis of two N-glycoside indoles 1 and 2, identified as highly potent sodium-dependent glucose transporter (SGLT) inhibitors is described. Highlights of the synthetic process include a selective and quantitative Vilsmeier acylation and a high-yielding Grignard coupling reaction. The chemistry developed has been applied to prepare two separate SGLT inhibitors 1 and 2 for clinical evaluation
描述了两种N-糖苷吲哚1和2的实用合成方法,已确定它们是高效的钠依赖性葡萄糖转运蛋白(SGLT)抑制剂。合成过程的重点包括选择性和定量的Vilsmeier酰化反应和高产率的Grignard偶联反应。已开发的化学方法已用于制备两种单独的SGLT抑制剂1和2,无需进行色谱分析即可用于临床评估。