Ethyl (3S,4aR,6S,8aR)-6-(4-ethoxycar- bonylimidazol-1-ylmethyl)decahydroiso-quinoline-3-carboxylic ester: a prodrug of a GluR5 kainate receptor antagonist active in two animal models of acute migraine

J Med Chem. 2002 Sep 26;45(20):4383-6. doi: 10.1021/jm025548q.

Abstract

Amino diacid 3, a highly selective competitive GluR5 kainate receptor antagonist, exhibited high GluR5 receptor affinity and selectivity over other glutamate receptors. Its diethyl ester prodrug 4 was orally active in two models of migraine: the neurogenic dural plasma protein extravasation model and the nucleus caudalis c-fos expression model. These data suggest that a GluR5 kainate receptor antagonist might be an efficacious antimigraine therapy with a novel mechanism of action.

MeSH terms

  • Acute Disease
  • Administration, Oral
  • Animals
  • Biological Availability
  • Calcium / metabolism
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / pharmacology
  • Cell Line
  • Disease Models, Animal
  • Dose-Response Relationship, Drug
  • Esters / chemical synthesis*
  • Esters / chemistry
  • Esters / pharmacology
  • Excitatory Amino Acid Antagonists / chemical synthesis*
  • Excitatory Amino Acid Antagonists / chemistry
  • Excitatory Amino Acid Antagonists / pharmacology
  • Humans
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry
  • Isoquinolines / pharmacology
  • Migraine Disorders / drug therapy*
  • Prodrugs / chemical synthesis*
  • Prodrugs / chemistry
  • Prodrugs / pharmacology
  • Radioligand Assay
  • Rats
  • Rats, Wistar
  • Receptors, Kainic Acid / antagonists & inhibitors*

Substances

  • 6-(4-carboxyimidazol-1-ylmethyl)decahydroisoquinoline-3-carboxylic acid
  • Carboxylic Acids
  • Esters
  • Excitatory Amino Acid Antagonists
  • Gluk1 kainate receptor
  • Isoquinolines
  • Prodrugs
  • Receptors, Kainic Acid
  • ethyl 6-(4-ethoxycarbonylimidazol-1-ylmethyl)decahydroisoquinoline-3-carboxylic ester
  • Calcium