Reaction of bis[(2-chlorocarbonyl)phenyl] Diselenide with Phenols, Aminophenols, and Other Amines towards Diphenyl Diselenides with Antimicrobial and Antiviral Properties

Molecules. 2017 Jun 12;22(6):974. doi: 10.3390/molecules22060974.

Abstract

A reaction of bis[(2-chlorocarbonyl)phenyl] diselenide with various mono and bisnucleophiles such as aminophenols, phenols, and amines have been studied as a convenient general route to a series of new antimicrobial and antiviral diphenyl diselenides. The compounds, particularly bis[2-(hydroxyphenylcarbamoyl)]phenyl diselenides and reference benzisoselenazol-3(2H)-ones, exhibited high antimicrobial activity against Gram-positive bacterial species (Enterococcus spp., Staphylococcus spp.), and some compounds were also active against Gram-negative E. coli and fungi (Candida spp., A.niger). The majority of compounds demonstrated high activity against human herpes virus type 1 (HHV-1) and moderate activity against encephalomyocarditis virus (EMCV), while they were generally inactive against vesicular stomatitis virus (VSV).

Keywords: 2-hydroxyacetanilide; antimicrobial activity; antimycin A; antiviral activity; benzisoselenazol-3(2H)-ones; benzohydrazide; diselenides; ebselen; morpholine; organoselenium compounds.

MeSH terms

  • Amines / chemical synthesis
  • Amines / chemistry
  • Aminophenols / chemical synthesis
  • Aminophenols / chemistry
  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Benzene Derivatives / chemical synthesis
  • Benzene Derivatives / chemistry
  • Benzene Derivatives / pharmacology*
  • Candida / drug effects
  • Candida / pathogenicity
  • Escherichia coli / drug effects
  • Escherichia coli / pathogenicity
  • Herpesvirus 1, Human / drug effects
  • Herpesvirus 1, Human / pathogenicity
  • Humans
  • Microbial Sensitivity Tests
  • Organoselenium Compounds / chemical synthesis
  • Organoselenium Compounds / chemistry
  • Organoselenium Compounds / pharmacology*
  • Phenols / chemical synthesis
  • Phenols / chemistry

Substances

  • Amines
  • Aminophenols
  • Anti-Infective Agents
  • Antifungal Agents
  • Antioxidants
  • Antiviral Agents
  • Benzene Derivatives
  • Organoselenium Compounds
  • Phenols
  • diphenyldiselenide