22 thioglycosides with novel structure were designed and synthesized from 5-substituded phenyloxymethyl-2-mercapto-1,3,4-thiadiazole and tetra-O-acetyl-α-glycopyranosyl bromides in the presence of phase transfer catalysis (BnEt₃N^＋Br^－) at room temperature. These compounds were characterized by IR, ¹H NMR, ¹³C NMR, and HR-ESI-MS techniques. Bioactivity of decreasing blood glucose was performed through in vivo by oral glucose tolerance test (OGTT) in mice. In addition, preliminary pharmacological test showed that compound 9Ah was more potent than positive control gliclazide, while compounds 9Aa and 9Bi were comparable to gliclazide in potency.

Key words: thiadiazole, thioglycoside, SGLT2 inhibitor, synthesis, anti-hyperglycemic activity