Synthesis and antimicrobial activities of silver(I) 3-(substituted phenyl)sulfanylpropenoates

Eur J Med Chem. 2008 Nov;43(11):2489-97. doi: 10.1016/j.ejmech.2008.07.011. Epub 2008 Jul 19.

Abstract

We investigated the reactions of silver nitrate with 3-(substituted phenyl)-2-sulfanylpropenoic acids H(2)L [L=xspa, where spa=2-sulfanylpropenoato and xin{Clp=3-(2-chlorophenyl)-, -o-mp=3-(2-methoxyphenyl)-, -o-hp=3-(2-hydroxyphenyl)-, -p-hp=3-(4-hydroxyphenyl)-, diBr-o-hp=3-(3,5-dibromo-2-hydroxyphenyl)-}] in 1:1 and 2:1 molar ratios. The 1:1 reactions gave compounds of type [Ag(HL)], which reacted with NaOH to afford Na[Ag(L)].xH(2)O (x=1 or 2) and with diisopropylamine to afford [HQ][Ag(L)] (HQ=diisopropylammonium). The 2:1 reactions gave products of type [Ag(2)(L)]. All the new compounds were isolated and characterized by IR spectroscopy, and all except the 2:1 adducts (which were insoluble) were studied by (1)H and (13)C NMR spectroscopy; ESI-MS spectrometry was also used for [HQ][Ag(L)] and Na[Ag(L)].xH(2)O, and the crystal structures of H(2)Clpspa and [HQ][Ag(Clpspa)] were determined by X-ray diffractometry. The antimicrobial activities of the complexes against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Candida albicans, Pseudomonas aeruginosa and carbapenem-resistant P. aeruginosa were evaluated and compared with those of Ag(I) complexes with other aryl sulfanylpropenoates or related ligands.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Microbial Viability / drug effects
  • Models, Molecular
  • Molecular Structure
  • Propane / chemical synthesis*
  • Propane / chemistry
  • Propane / pharmacology*
  • Silver Compounds / chemical synthesis*
  • Silver Compounds / chemistry
  • Silver Compounds / pharmacology*
  • Spectrophotometry, Infrared
  • Sulfur Compounds / chemical synthesis*
  • Sulfur Compounds / chemistry
  • Sulfur Compounds / pharmacology

Substances

  • Anti-Bacterial Agents
  • Silver Compounds
  • Sulfur Compounds
  • Propane