Synthesis and biological evaluation of imidazol-2-one and 2-cyanoiminoimidazole derivatives: novel series of PDE4 inhibitors

Bioorg Med Chem Lett. 2002 Feb 25;12(4):653-8. doi: 10.1016/s0960-894x(01)00817-4.

Abstract

This communication describes the synthesis and in vitro PDE4 inhibitory activity of a novel series of imidazol-2-one and 2-cyanoiminoimidazole derivatives. The compounds described were also tested in in vivo models to evaluate their anti-inflammatory activity after topical administration as well as their gastro-intestinal side effects. Several compounds proved to be potent PDE4 inhibitors and some 2-cyanoiminoimidazoles showed less pronounced gastro-intestinal side effects than reference compounds but maintained anti-inflammatory activity after topical administration.

MeSH terms

  • 3',5'-Cyclic-AMP Phosphodiesterases / antagonists & inhibitors*
  • Administration, Topical
  • Animals
  • Anti-Inflammatory Agents / administration & dosage
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / pharmacology
  • Cyclic Nucleotide Phosphodiesterases, Type 4
  • Disease Models, Animal
  • Dose-Response Relationship, Drug
  • Ear Diseases / drug therapy
  • Enzyme Inhibitors / administration & dosage
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Imidazoles / administration & dosage
  • Imidazoles / chemical synthesis
  • Imidazoles / pharmacology*
  • Inflammation / drug therapy
  • Inhibitory Concentration 50
  • Rats
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents
  • Enzyme Inhibitors
  • Imidazoles
  • imidazolone
  • 3',5'-Cyclic-AMP Phosphodiesterases
  • Cyclic Nucleotide Phosphodiesterases, Type 4