Reactions of Nitroxides, Part 17. Synthesis, Fungistatic and Bacteriostatic Activity of Novel Five- and Six-Membered Nitroxyl Selenoureas and Selenocarbamates

Molecules. 2019 Jul 4;24(13):2457. doi: 10.3390/molecules24132457.

Abstract

The reactions of 3-isoselenocyanato-2,2,5,5-tetramethylpyrrolidine-1-oxyl, 3-isoselenocyanatomethyl-2,2,5,5-tetramethyl-3-pyrrolidine-1-oxyl, and 4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl with selected amines and alcohols give the corresponding novel nitroxyl selenoureas and selenocarbamates, all bearing a nitroxyl moiety. Synthesized selenoureas and selenocarbamates show significant activity against pathogenic fungi and bacteria. In contrast to piperidine nitroxides, pyrrolidine, five-membered nitroxyl selenoureas and selenocarbamates show excellent antifungal and antibacterial activity against pathogenic fungi and bacteria, respectively.

Keywords: bacteriostatic activity; fungistatic activity; organoselenium compounds; selenocarbamates; selenoureas.

MeSH terms

  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / pharmacology*
  • Bacteria / drug effects
  • Carbamates / chemical synthesis
  • Carbamates / chemistry
  • Carbamates / pharmacology*
  • Fungi / drug effects
  • Microbial Sensitivity Tests
  • Nitrogen Oxides / chemical synthesis*
  • Nitrogen Oxides / chemistry
  • Nitrogen Oxides / pharmacology*
  • Organoselenium Compounds / chemical synthesis
  • Organoselenium Compounds / chemistry
  • Organoselenium Compounds / pharmacology*
  • Urea / analogs & derivatives*
  • Urea / chemical synthesis
  • Urea / chemistry
  • Urea / pharmacology

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Carbamates
  • Nitrogen Oxides
  • Organoselenium Compounds
  • selenourea
  • Urea
  • nitroxyl