Design, synthesis, and biological evaluation of new phosphodiesterase type 4 inhibitors

Bioorg Med Chem. 2004 Oct 1;12(19):5063-78. doi: 10.1016/j.bmc.2004.07.040.

Abstract

The design, synthesis, and biological evaluation of new phosphodiesterase type 4 inhibitors, which possess new templates instead of a cyclohexane ring, are described. The mode of interaction with the enzyme is discussed based on the structure-activity relationship (SAR) data obtained for the synthesized inhibitors. Furthermore, the roles of three pharmacophores, a catechol moiety, a nitrile moiety, and acidic moieties, are discussed using in silico docking studies. More detailed biological evaluations of selected compounds are also presented.

MeSH terms

  • 3',5'-Cyclic-AMP Phosphodiesterases / antagonists & inhibitors*
  • Animals
  • Binding Sites
  • Bronchoconstriction / drug effects
  • Computer Simulation
  • Cyclic Nucleotide Phosphodiesterases, Type 4
  • Drug Design
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Ferrets
  • Gastric Emptying / drug effects
  • Guinea Pigs
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Heterocyclic Compounds, 4 or More Rings / pharmacology
  • Male
  • Rats
  • Rats, Sprague-Dawley
  • Rolipram / chemistry
  • Structure-Activity Relationship
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors
  • Tumor Necrosis Factor-alpha / biosynthesis
  • Vomiting / drug therapy

Substances

  • Enzyme Inhibitors
  • Heterocyclic Compounds, 4 or More Rings
  • Tumor Necrosis Factor-alpha
  • 3',5'-Cyclic-AMP Phosphodiesterases
  • Cyclic Nucleotide Phosphodiesterases, Type 4
  • Rolipram