Inhibitors of glycolic acid oxidase. 4-substituted 2,4-dioxobutanoic acid derivatives

J Med Chem. 1983 Aug;26(8):1196-200. doi: 10.1021/jm00362a020.

Abstract

Fourteen new 4-substituted 2,4-dioxobutanoic acids have been synthesized. These compounds, all of which contain lipophilic 4-substituents, are potent inhibitors in vitro of porcine liver glycolic acid oxidase. The I50 value of the two most potent representatives, 4-(4'-bromo[1,1'-biphenyl]-4-yl)-2, 4-dioxobutanoic acid (8) and 4-[4'-[[(3,4-dihydro-3-hydroxy-2H-1, 5-benzodioxepin-3-yl)methyl]thio][1,1'-biphenyl]-4-yl]-2, 4-dioxobutanoic acid (13) is 6 X 10(-8)M.

MeSH terms

  • Alcohol Oxidoreductases / antagonists & inhibitors*
  • Biphenyl Compounds
  • Butyrates / chemical synthesis*
  • Butyrates / pharmacology
  • Oxepins

Substances

  • Biphenyl Compounds
  • Butyrates
  • Oxepins
  • 4-(4'-bromo(1,1'-biphenyl)-4-yl)-2,4-dioxobutanoic acid
  • 4-(4'-(((3,4-dihydro-3-hydroxy-2H-1,5-benzodioxepin-3-yl)methyl)thio)(1,1'-biphenyl)-4-yl)-2,4-dioxobutanoic acid
  • Alcohol Oxidoreductases
  • glycollate oxidase