Chromene-Containing Aromatic Sulfonamides with Carbonic Anhydrase Inhibitory Properties

Int J Mol Sci. 2021 May 11;22(10):5082. doi: 10.3390/ijms22105082.

Abstract

Carbonic anhydrases (CAs, EC 4.2.1.1) catalyze the essential reaction of CO2 hydration in all living organisms, being actively involved in the regulation of a plethora of patho/physiological conditions. A series of chromene-based sulfonamides were synthesized and tested as possible CA inhibitors. Their inhibitory activity was assessed against the cytosolic human isoforms hCA I, hCA II and the transmembrane hCA IX and XII. Several of the investigated derivatives showed interesting inhibition activity towards the tumor associate isoforms hCA IX and hCA XII. Furthermore, computational procedures were used to investigate the binding mode of this class of compounds, within the active site of hCA IX.

Keywords: Chromene; carbonic anhydrase; inhibitors; metalloenzymes.

MeSH terms

  • Benzopyrans / chemistry*
  • Carbonic Anhydrase Inhibitors / chemistry
  • Carbonic Anhydrase Inhibitors / pharmacology*
  • Carbonic Anhydrases / chemistry*
  • Catalytic Domain
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Structure-Activity Relationship
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*

Substances

  • Benzopyrans
  • Carbonic Anhydrase Inhibitors
  • Sulfonamides
  • Carbonic Anhydrases