Synthesis and in vitro evaluation of 12-(substituted aminomethyl) berberrubine derivatives as anti-diabetics

Bioorg Med Chem Lett. 2014 Apr 1;24(7):1762-5. doi: 10.1016/j.bmcl.2014.02.032. Epub 2014 Feb 21.

Abstract

By introducing various amino methyl groups into 12-position of berberrubine, a series of 12-(substituted aminomethyl) berberrubine derivatives were synthesized and evaluated for their anti-diabetic activity against type 2 diabetes mellitus. The results indicated that most of the prepared compounds exhibited moderate to good anti-diabetic activity, which were comparable to or even better than the berberine, the positive control rosiglitazone and insulin. Especially, compound 3b with an N-methyl piperazine-4-methyl group at C-12, exerted the most powerful anti-diabetic activity.

Keywords: 12-(Substituted aminomethyl) berberrubine derivatives; Anti-diabetic activity; Synthesis; Type 2 diabetes mellitus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3T3-L1 Cells
  • Adipocytes / drug effects*
  • Animals
  • Berberine / analogs & derivatives*
  • Berberine / chemical synthesis
  • Berberine / chemistry
  • Berberine / pharmacology
  • Diabetes Mellitus, Type 2 / drug therapy*
  • Diabetes Mellitus, Type 2 / pathology
  • Dose-Response Relationship, Drug
  • Glucose / pharmacokinetics
  • Hypoglycemic Agents / chemical synthesis
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / pharmacology*
  • Insulin Resistance
  • Mice
  • Molecular Structure
  • Muscle Fibers, Skeletal / drug effects*
  • Rats
  • Structure-Activity Relationship

Substances

  • Hypoglycemic Agents
  • Berberine
  • berberrubine
  • Glucose