Aglycone exploration of C-arylglucoside inhibitors of renal sodium-dependent glucose transporter SGLT2.
2008
Abstract Inhibition of sodium-dependent glucose transporter 2 (SGLT2), the transporter that is responsible for renal re-uptake of glucose, leads to glucosuria in animals. SGLT-mediated glucosuria provides a mechanism to shed excess plasma glucose to ameliorate diabetes-related hyperglycemia and associated complications. The current study demonstrates that the proper relationship of a 4′-substituted benzyl group to a β- 1C -phenylglucoside is important for potent and selective SGLT2 inhibition. The lead C -arylglucoside ( 7a ) demonstrates superior metabolic stability to its O -arylglucoside counterpart ( 4 ) and it promotes glucosuria when administered in vivo.
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