Synthesis and evaluation of sulfonium-type alpha-glucosidase inhibitors based on the structure of salacinol

点击翻译按钮获取中文摘要

To develop more potent alpha-glucosidase inhibitors whose seed-compound is salacinol (1), a potent natural alpha-glucosidase inhibitor isolated from Salacia reticulata of Ayurvedic traditional medicine, several candidates with 3'-O-alkyl (CH3, C2H5, C13H27) or benzyl groups (CH2C6H5, CH2C6H4CH3, CH2C6H5Cl, CH2C6H4CF3, CH2C6H4NO2) instead of the 3'-O-sulfate anion in 1 were synthesized. These analogs showed equal or considerably higher inhibitory activity against rat small intestinal alpha-glucosidases than 1. Among the sulfonium salts designed, one with 3'-O-(ortho-nitrobenzyl) moiety was found to be the most potent, and ca. forty times as potent as 1, the compound being the strongest inhibitor among the sulfonium type inhibitors synthesized so far.