SAR-study on a new class of imidazo[1,2-a]pyridine-based inhibitors of 5-lipoxygenase

Bioorg Med Chem Lett. 2012 Mar 1;22(5):1969-75. doi: 10.1016/j.bmcl.2012.01.038. Epub 2012 Jan 24.

Abstract

A novel class of 5-lipoxygenase (5-LO) inhibitors characterized by a central imidazo[1,2-a]pyridine scaffold, a cyclohexyl moiety and an aromatic system, is presented. This scaffold was identified in a virtual screening study and exhibits promising inhibitory potential on the 5-LO. Here, we investigate the structure-activity relationships of this compound class. With N-cyclohexyl-6-methyl-2-(4-morpholinophenyl)imidazo[1,2-a]pyridine-3-amine (14), we identified a potent 5-LO inhibitor (IC(50)=0.16μM (intact cells) and 0.1μM (cell-free)), which may possess potential as an effective lead compound intervening with inflammatory diseases and certain types of cancer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemical synthesis
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology
  • Arachidonate 5-Lipoxygenase / metabolism*
  • Humans
  • Leukocytes / drug effects
  • Leukocytes / enzymology
  • Lipoxygenase Inhibitors / chemical synthesis
  • Lipoxygenase Inhibitors / chemistry*
  • Lipoxygenase Inhibitors / pharmacology*
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*
  • Pyridines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents
  • Lipoxygenase Inhibitors
  • Pyridines
  • Arachidonate 5-Lipoxygenase
  • imidazo(1,2-a)pyridine