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

Debasis Das; Gouriprasanna Roy; Govindasamy Mugesh

doi:10.1021/jm800894m

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.

Authors

Debasis Das¹, Gouriprasanna Roy, Govindasamy Mugesh

Affiliation

¹ Department of Inorganic & Physical Chemistry, Indian Institute of Science, Bangalore 560 012, India.

PMID: 18954039
DOI: 10.1021/jm800894m

Abstract

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*

Substances

Antithyroid Agents
Tyrosine
Carbimazole
Peroxidase