New 4-[(3-cyclohexyl-4-aryl-2,3-dihydro-1,3-thiazol-2-ylidene)amino]benzene-1-sulfonamides, synthesis and inhibitory activity toward carbonic anhydrase I, II, IX, XII

Bioorg Med Chem Lett. 2015 Aug 15;25(16):3281-4. doi: 10.1016/j.bmcl.2015.05.076. Epub 2015 May 30.

Abstract

A series of 4-[(3-cyclohexyl-4-aryl-2,3-dihydro-1,3-thiazol-2-ylidene)amino]benzene-1-sulfonamides was synthesised and the activity of the new compounds as inhibitors of hCA I, II, IX, and XII was evaluated. These new derivatives exhibited some peculiarities with respect to previously reported sulfonamide based inhibitors of CA. We observed that the nature of the substituents in the position 3 and 4 of the dihydro-thiazole ring was relevant in determining both activity and selectivity profiles.

Keywords: Carbonic anhydrase; Selective inhibitor; Sulfonamide; Tumor-associated isoform.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzenesulfonamides
  • Binding Sites
  • Carbonic Anhydrase I / antagonists & inhibitors*
  • Carbonic Anhydrase II / antagonists & inhibitors*
  • Carbonic Anhydrase Inhibitors / chemical synthesis
  • Carbonic Anhydrase Inhibitors / chemistry
  • Carbonic Anhydrase Inhibitors / pharmacology
  • Carbonic Anhydrases / metabolism*
  • Enzyme Activation / drug effects
  • Humans
  • Isoenzymes / chemical synthesis
  • Isoenzymes / chemistry
  • Isoenzymes / pharmacology
  • Models, Biological
  • Molecular Structure
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry
  • Thiazoles / pharmacology
  • Triazoles / chemical synthesis
  • Triazoles / chemistry
  • Triazoles / pharmacology

Substances

  • Carbonic Anhydrase Inhibitors
  • EMAC 8001l
  • Isoenzymes
  • Sulfonamides
  • Thiazoles
  • Triazoles
  • 1,2,4-triazole
  • Carbonic Anhydrase I
  • Carbonic Anhydrase II
  • Carbonic Anhydrases