Inhibition of estrone sulfatase (ES) by alkyl and cycloalkyl ester derivatives of 4-[(aminosulfonyl)oxy] benzoic acid

Bioorg Med Chem Lett. 2004 Feb 9;14(3):605-9. doi: 10.1016/j.bmcl.2003.11.067.

Abstract

In our search for potent inhibitors of the enzyme estrone sulfatase (ES), we have undertaken the synthesis and biochemical evaluation of a range of esters of 4-[(aminosulfonyl)oxy] benzoic acid. The results of the study show that the synthesised compounds possess potent inhibitory activity, indeed the cyclooctyl derivative was found to be more potent than 667-COUMATE, which is currently undergoing clinical trials.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology
  • Benzoic Acid / chemical synthesis
  • Benzoic Acid / chemistry
  • Benzoic Acid / pharmacology*
  • Coumarins / pharmacology
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology*
  • Esters
  • Inhibitory Concentration 50
  • Structure-Activity Relationship
  • Sulfatases / antagonists & inhibitors*
  • Sulfonamides / pharmacology
  • Sulfonic Acids

Substances

  • Antineoplastic Agents
  • Coumarins
  • Enzyme Inhibitors
  • Esters
  • Sulfonamides
  • Sulfonic Acids
  • irosustat
  • Benzoic Acid
  • sulfamic acid
  • Sulfatases
  • estrone sulfatase