Antithyroid drug carbimazole and its analogues: synthesis and inhibition of peroxidase-catalyzed iodination of L-tyrosine

J Med Chem. 2008 Nov 27;51(22):7313-7. doi: 10.1021/jm800894m.


Synthesis and biological activity of the antithyroid drug carbimazole (CBZ) and its analogues are described. The introduction of an ethoxycarbonyl group in methimazole and its selenium analogue not only prevents the oxidation to the corresponding disulfide and diselenide but also reduces the zwitterionic character. A structure-activity correlation in a series of CBZ analogues suggests that the presence of a methyl substituent in CBZ and related compounds is important for their antithyroid activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antithyroid Agents / chemical synthesis*
  • Antithyroid Agents / chemistry
  • Antithyroid Agents / pharmacology*
  • Carbimazole / analogs & derivatives*
  • Carbimazole / chemistry
  • Carbimazole / pharmacology*
  • Catalysis / drug effects
  • Computer Simulation
  • Halogenation / drug effects
  • Molecular Structure
  • Peroxidase / antagonists & inhibitors*
  • Peroxidase / metabolism
  • Structure-Activity Relationship
  • Tyrosine / chemistry
  • Tyrosine / metabolism*


  • Antithyroid Agents
  • Tyrosine
  • Carbimazole
  • Peroxidase