Synthesis of Schiff base derivatives of 4-(2-aminoethyl)-benzenesulfonamide with inhibitory activity against carbonic anhydrase isoforms I, II, IX and XII

Bioorg Med Chem Lett. 2015 Jun 1;25(11):2377-81. doi: 10.1016/j.bmcl.2015.04.007. Epub 2015 Apr 10.

Abstract

Schiff base derivatives were obtained by reaction of 4-(2-aminoethyl)benzenesulfonamide with aromatic aldehydes. The corresponding secondary amine derivatives were also prepared by reduction of the imine compounds with NaBH4. These derivatives were investigated as inhibitors of four human carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the cytosolic isozymes hCA I and II, as well as, the transmembrane, tumor-associated hCA IX and XII. Some of the newly synthesised compounds showed effective inhibitory activities against these CA isozymes. Many low nanomolar inhibitors were detected against all isoforms among the secondary amines whereas the Schiff bases were by far less active compared to the corresponding reduced derivatives among all investigated isoforms.

Keywords: Carbonic anhydrase; Inhibitor; Schiff base; Secondary amine; Sulfonamide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbonic Anhydrase Inhibitors / chemistry*
  • Carbonic Anhydrase Inhibitors / pharmacology*
  • Carbonic Anhydrases / classification*
  • Imines / chemistry
  • Imines / pharmacology
  • Isoenzymes / antagonists & inhibitors
  • Molecular Structure
  • Sulfonamides / chemistry*

Substances

  • Carbonic Anhydrase Inhibitors
  • Imines
  • Isoenzymes
  • Sulfonamides
  • Carbonic Anhydrases