Synthesis and Antimicrobial Properties of Novel Phosphonium Salts Bearing 1,4-Dihydroxyaryl Fragment

Chem Biodivers. 2019 May;16(5):e1900039. doi: 10.1002/cbdv.201900039. Epub 2019 Apr 10.

Abstract

A versatile two-step pathway to the synthesis of triaryl(2,5-dihydroxy-6-methyl-3-(propan-2-yl)phenyl)- and triaryl(1,4-dihydroxynaphthyl)phosphonium salts from triarylphosphonium trifluoroacetates was developed. The reaction proceeds under mild conditions (20 °C, CH2 Cl2 ) with high yields (88-95 %). Some representatives of this series possess low hemolytic and high bactericidal activity against Gram-positive bacteria.

Keywords: 1,4-naphthoquinone; H-phosphonium salt; antibacterial activity; synthesis design; tertiary phosphine; tetraarylphosphonium salt; thymoquinone.

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / pharmacology
  • Fungi / drug effects
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Microbial Sensitivity Tests
  • Naphthoquinones / chemistry
  • Organophosphorus Compounds / chemistry*
  • Organophosphorus Compounds / pharmacology
  • Salts / chemistry

Substances

  • Anti-Infective Agents
  • Naphthoquinones
  • Organophosphorus Compounds
  • Salts