Synthesis and carbonic anhydrase inhibitory properties of novel chalcone substituted benzenesulfonamides

Bioorg Med Chem Lett. 2016 Dec 15;26(24):5867-5870. doi: 10.1016/j.bmcl.2016.11.017. Epub 2016 Nov 9.

Abstract

Carbonic anhydrases (CAs, EC 4.2.1.1) are crucial metalloenzymes involved in many bioprocesses, through catalysis of the reversible hydration/dehydration process of CO2/HCO3-. The inhibition of human CA isoforms I and II with a new series of sulfonamide derivatives incorporating substituted chalcone moieties were studied in this study. All these newly synthesized sulfonamides demonstrated important inhibitory profiles to these CA isoforms with KIs in the range of 9.88 to 55.43nM, making these compounds interesting leads, with potential applications in medicinal chemistry.

Keywords: Carbonic anhydrase; Chalcone; Inhibitors; Sulfonamides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzenesulfonamides
  • Carbonic Anhydrase I / metabolism*
  • Carbonic Anhydrase II / metabolism*
  • Carbonic Anhydrase Inhibitors / chemical synthesis
  • Carbonic Anhydrase Inhibitors / chemistry
  • Carbonic Anhydrase Inhibitors / pharmacology*
  • Chalcone / chemistry
  • Chalcone / pharmacology*
  • Dose-Response Relationship, Drug
  • Humans
  • Molecular Structure
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*

Substances

  • Carbonic Anhydrase Inhibitors
  • Sulfonamides
  • Chalcone
  • Carbonic Anhydrase I
  • Carbonic Anhydrase II