Tricyclic heteroaromatic systems: [1]benzopyrano-pyrazol-4-ones as benzodiazepine receptor ligands

J Pharm Sci. 1991 Mar;80(3):276-9. doi: 10.1002/jps.2600800317.

Abstract

The synthesis of a series of 8-substituted 1,4-dihydro-1-aryl-3-methyl-[1]benzopyrano[3,4-d]pyrazol-4-ones (series 7) 2,4-dihydro-2-aryl-3-methyl[1]benzopyrano[4,3-c]pyrazol-4-ones (series 8) is reported. Compounds of series 7 and 8 were tested for their ability to displace [3H]flunitrazepam from bovine brain membranes and for their in vitro biological activity. The results allowed some conclusions to be drawn about the structural requirements of the benzodiazepine recognition site within this class of unusual ligands.

MeSH terms

  • Animals
  • Benzopyrans / chemical synthesis*
  • Benzopyrans / pharmacology
  • Binding, Competitive / drug effects
  • Cattle
  • Flunitrazepam / metabolism
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / pharmacology*
  • In Vitro Techniques
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / pharmacology
  • Receptors, GABA-A / drug effects*
  • Structure-Activity Relationship
  • gamma-Aminobutyric Acid / metabolism

Substances

  • Benzopyrans
  • Heterocyclic Compounds
  • Pyrazoles
  • Receptors, GABA-A
  • gamma-Aminobutyric Acid
  • Flunitrazepam