Microwave assisted synthesis of novel tetrazole/sulfonamide derivatives based on octahydroacridine, xanthene and chromene skeletons as inhibitors of the carbonic anhydrases isoforms I, II, IV and VII

Bioorg Med Chem Lett. 2017 Jan 1;27(1):86-89. doi: 10.1016/j.bmcl.2016.11.028. Epub 2016 Nov 12.

Abstract

The synthesis of novel tetrazole/sulfonamide derivatives based on octahydroacridine, xanthene and chromene scaffold by using microwave (MW) assisted techniques is reported in this study. These synthesized hybrid compounds were assayed for the inhibition of carbonic anhydrase (CA, EC 4.2.1.1). The inhibitory activities were determined against three cytosolic human isoforms (hCA I, II and VII) and one membrane-associated (hCA IV) isoform. Some of the newly synthesized sulfonamides showed micromolar to nanomolar inhibitory activity against these enzymes.

Keywords: Carbonic anhydrase; Chromene; Enzyme inhibition; Octahydroacridine; Sulfonamide; Tetrazole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridines / chemistry
  • Acridines / pharmacology
  • Benzopyrans / chemistry
  • Benzopyrans / pharmacology
  • Carbonic Anhydrase Inhibitors / chemical synthesis
  • Carbonic Anhydrase Inhibitors / chemistry
  • Carbonic Anhydrase Inhibitors / pharmacology*
  • Carbonic Anhydrases / metabolism*
  • Dose-Response Relationship, Drug
  • Humans
  • Isoenzymes / antagonists & inhibitors
  • Isoenzymes / metabolism
  • Microwaves*
  • Molecular Structure
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*
  • Tetrazoles / chemical synthesis
  • Tetrazoles / chemistry
  • Tetrazoles / pharmacology*
  • Xanthenes / chemistry
  • Xanthenes / pharmacology

Substances

  • 1,2,3,4,5,6,7,8-octahydroacridine
  • Acridines
  • Benzopyrans
  • Carbonic Anhydrase Inhibitors
  • Isoenzymes
  • Sulfonamides
  • Tetrazoles
  • Xanthenes
  • Carbonic Anhydrases