A Concise Synthesis of Potential COX Inhibitor BRL-37959 and Analogs Involving Bismuth(III) Catalyzed Friedel-Crafts Acylation

Chem Biodivers. 2018 Dec;15(12):e1800334. doi: 10.1002/cbdv.201800334. Epub 2018 Nov 22.

Abstract

We report the development of a concise method of synthesizing possible cyclooxygenase (COX) inhibitor BRL-37959, which is believed to be a potent nonsteroidal anti-inflammatory drug (NSAID). The four-step synthesis greatly increased the efficiency of compound production from commercially available salicylaldehydes. The synthesis involved an optimized, bismuth(III) trifluoromethanesulfonate catalyzed benzoylation of a benzofuran ring.

Keywords: NSAID; benzofuran; benzoylation; bismuth(III) trifluoromethanesulfonate; synthesis design.

MeSH terms

  • Acylation
  • Aldehydes / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Benzofurans / chemistry
  • Bismuth / chemistry*
  • Catalysis
  • Cyclooxygenase Inhibitors / chemical synthesis
  • Cyclooxygenase Inhibitors / chemistry*
  • Microwaves
  • Temperature

Substances

  • Aldehydes
  • Anti-Inflammatory Agents, Non-Steroidal
  • Benzofurans
  • Cyclooxygenase Inhibitors
  • salicylaldehyde
  • benzofuran
  • Bismuth