Novel arylazoarylmethane as potential inhibitor of macrophage migration inhibitory factor

Arch Pharm (Weinheim). 2014 Feb;347(2):104-7. doi: 10.1002/ardp.201300243. Epub 2013 Nov 18.

Abstract

Macrophage migration inhibitory factor (MIF), a cytokine involved in the pathogenesis of sepsis, diabetes, asthma, arthritis, and cancer, has an enzymatic active site that has proven to be an effective target for small molecule-based inhibitors. Herein, we describe the synthesis of a novel arylazoarylmethane compound (3) from a known arylhydrazone MIF inhibitor (2). This new compound has improved stability and in vivo biological activity.

Keywords: Arylazoarylmethane; Arylhydrazone; Inflammation; Macrophage migration inhibitory factor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / pharmacology*
  • Carrageenan
  • Disease Models, Animal
  • Drug Design
  • Drug Stability
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Hydrazones / chemical synthesis*
  • Hydrazones / pharmacology*
  • Inflammation / chemically induced
  • Inflammation / enzymology
  • Inflammation / prevention & control
  • Intramolecular Oxidoreductases / antagonists & inhibitors
  • Intramolecular Oxidoreductases / metabolism
  • Macrophage Migration-Inhibitory Factors / antagonists & inhibitors*
  • Macrophage Migration-Inhibitory Factors / metabolism
  • Mice
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents
  • Enzyme Inhibitors
  • Hydrazones
  • Macrophage Migration-Inhibitory Factors
  • Carrageenan
  • Intramolecular Oxidoreductases
  • Mif protein, mouse