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Synthesis, Characterization, and Biological Evaluations of 1,3,5-Triazine Derivatives of Metformin Cyclization with Berberine and Magnolol in the Presence of Sodium Methylate

Molecules. 2017 Oct 18;22(10):1752. doi: 10.3390/molecules22101752.

Abstract

The novel target products were synthesized in the formation of a triazine ring from berberine, magnolol, and metformin catalyzed by sodium methylate. The structures of products 1-3 were firstly confirmed by extensive spectroscopic analyses and single-crystal X-ray diffraction. The crystal structures of the target product 2 and the intermediate product 7b were reported for the first time. All target products were evaluated for their anti-inflammatory and antidiabetic activities against INS-1 and RAW264.1 cells in vitro and all products showed excellent anti-inflammatory effects and anti-insulin resistance effects. Our studies indicated that new compounds 1-3 were found to be active against inflammation and insulin resistance.

Keywords: anti-inflammatory activity; anti-insulin resistance; cyclization triazine.

MeSH terms

  • Anti-Inflammatory Agents / chemical synthesis
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology*
  • Berberine / chemical synthesis
  • Berberine / chemistry
  • Biphenyl Compounds / chemical synthesis
  • Biphenyl Compounds / chemistry
  • Cyclization
  • Humans
  • Inflammation / drug therapy*
  • Insulin Resistance
  • Lignans / chemical synthesis
  • Lignans / chemistry
  • Metformin / analogs & derivatives
  • Metformin / chemistry
  • Metformin / pharmacology*
  • Molecular Structure
  • Sodium / chemistry
  • Structure-Activity Relationship
  • Triazines / chemical synthesis
  • Triazines / chemistry
  • Triazines / pharmacology*

Substances

  • Anti-Inflammatory Agents
  • Biphenyl Compounds
  • Lignans
  • Triazines
  • magnolol
  • Berberine
  • Metformin
  • Sodium