2-Mercaptobenzoxazoles: a class of carbonic anhydrase inhibitors with a novel binding mode to the enzyme active site

Chem Commun (Camb). 2020 Jul 23;56(59):8297-8300. doi: 10.1039/d0cc02857f.

Abstract

2-Mercaptobenzoxazole is a widely used organic scaffold in medicinal chemistry. By means of kinetic and structural studies, we demonstrate that this molecule can effectively be used to inhibit hCAs showing a peculiar binding mode. The results reported here can pave the way for the development of selective CA inhibitors.

MeSH terms

  • Amino Acid Sequence
  • Benzoxazoles / chemistry*
  • Benzoxazoles / metabolism
  • Carbonic Anhydrase Inhibitors / chemistry*
  • Carbonic Anhydrase Inhibitors / metabolism
  • Carbonic Anhydrases / metabolism*
  • Catalytic Domain
  • Humans
  • Kinetics
  • Models, Molecular
  • Protein Binding
  • Protein Conformation
  • Structure-Activity Relationship
  • Sulfhydryl Compounds / chemistry*
  • Sulfhydryl Compounds / metabolism

Substances

  • Benzoxazoles
  • Carbonic Anhydrase Inhibitors
  • Sulfhydryl Compounds
  • 2-mercaptobenzoxazole
  • Carbonic Anhydrases