Inhibitory effect of novel pyrazole carboxamide derivatives on human carbonic anhydrase enzyme

J Enzyme Inhib Med Chem. 2013 Apr;28(2):328-36. doi: 10.3109/14756366.2011.651465. Epub 2012 Feb 3.

Abstract

The synthesis, characterization and biological evaluation of novel pyrazole carboxamide derivatives (2-9) are presented. (1)H and (13)C NMR have been used for the structure description, possible tautomeric structures determination and hydrogen bonding observation. FT-IR results have confirmed the synthesis of the pyrazole derivatives while thermal gravimetric analysis has confirmed thermal stability up to 300°C. The melting temperatures are strongly dependent on their crystal structure as confirmed by differential scanning calorimetry and X-ray diffraction measurements. Impacts of 2-9 as possible antiglaucoma agents were investigated on carbonic anhydrase I and II (CA-I and II) isozymes purified from human erythrocytes in vitro. Compounds 3 and 9 had the highest inhibitory effect while compounds 6 and 8 showed the lowest inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbonic Anhydrase Inhibitors / chemical synthesis
  • Carbonic Anhydrase Inhibitors / chemistry
  • Carbonic Anhydrase Inhibitors / pharmacology*
  • Carbonic Anhydrases / isolation & purification
  • Carbonic Anhydrases / metabolism*
  • Dose-Response Relationship, Drug
  • Erythrocytes / enzymology
  • Humans
  • Molecular Structure
  • Protein Isoforms / antagonists & inhibitors
  • Protein Isoforms / isolation & purification
  • Protein Isoforms / metabolism
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Structure-Activity Relationship

Substances

  • Carbonic Anhydrase Inhibitors
  • Protein Isoforms
  • Pyrazoles
  • Carbonic Anhydrases