C-Aryl Glucosides with Substituents at the Distal Aryl Ring as Sodium-Dependent Glucose Cotransporter Inhibitors for the Treatment of Diabetes Mellitus

Chem Biol Drug Des. 2015 Aug;86(2):246-53. doi: 10.1111/cbdd.12487. Epub 2014 Dec 18.

Abstract

A series of novel C-aryl glucosides with various substituents at the distal aryl ring have been synthesized and evaluated for hypoglycemic effect in normal and diabetic mice and in type 2 diabetic rats. The results indicated that introduction of electron-donating group at the distal aryl ring could improve glucose tolerance in normal mice, whereas introduction of electron-withdrawing group at this position could deteriorate. The urinary glucose excretion was significantly increased after glucose (3 g/kg) administration in normal mice with the treatment of 13c. Moreover, compound 13c could reduce fed blood glucose levels in a dose-dependent manner in type 2 diabetic rats, showed a remarkable antihyperglycemic effect with 2 weeks of treatment in diabetic mice, and might be a promising drug candidate for the treatment of diabetes mellitus.

Keywords: C-aryl glucosides; diabetes mellitus type 2; sodium-glucose cotransporters.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Blood Glucose / metabolism
  • Diabetes Mellitus, Experimental / drug therapy
  • Diabetes Mellitus, Experimental / metabolism
  • Diabetes Mellitus, Type 2 / drug therapy*
  • Diabetes Mellitus, Type 2 / metabolism
  • Drug Design
  • Glucosides / chemistry
  • Glucosides / pharmacology*
  • Glycosuria / metabolism
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / pharmacology*
  • Male
  • Mice
  • Random Allocation
  • Rats
  • Rats, Sprague-Dawley
  • Sodium-Glucose Transport Proteins / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • Blood Glucose
  • Glucosides
  • Hypoglycemic Agents
  • Sodium-Glucose Transport Proteins