A new antibacterial silver(I) complex incorporating 2,5-dimethylpyrazine and the anti-inflammatory diclofenac

Acta Crystallogr C Struct Chem. 2016 Dec 1;72(Pt 12):947-951. doi: 10.1107/S2053229616017009. Epub 2016 Nov 4.

Abstract

AgI-containing coordination complexes have attracted attention because of their photoluminescence properties and antimicrobial activities and, in principle, these properties depend on the nature of the structural topologies. A novel two-dimensional silver(I) complex with the anti-inflammatory diclofenac molecule, namely bis{μ-2-[2-(2,6-dichloroanilino)phenyl]acetato-κ3O,O':O}bis(μ-2,5-dimethylpyrazine-κ2N:N')silver(I), [Ag2(C14H10Cl2NO2)2(C6H8N2)]n, (I), has been synthesized and characterized by single-crystal X-ray diffraction, revealing that the AgI ions are chelated by the carboxylate groups of the anionic 2-[2-(2,6-dichloroanilino)phenyl]acetate (dicl) ligand in a μ312 coordination mode. Each dicl ligand links three AgI atoms to generate a one-dimensional infinite chain. Adjacent chains are connected through 2,5-dimethylpyrazine (dmpyz) ligands to form a two-dimensional layer structure parallel to the crystallographic bc plane. The layers are further connected by C-H...π interactions to generate a three-dimensional supramolecular structure. Additionally, the most striking feature is that the structure contains an intramolecular C-H ...Ag anagostic interaction. Furthermore, the title complex has been tested for its in vitro antibacterial activity and is determined to be highly effective on the studied microorganisms.

Keywords: anagostic interaction; anti-inflammatory agent; antibacterial activity; crystal structure; diclofenac; silver(I) complex; two-dimensional coordination polymer.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Bacteria / drug effects
  • Chelating Agents / chemistry
  • Crystallography, X-Ray
  • Diclofenac / chemistry*
  • Diclofenac / pharmacology
  • Hydrogen Bonding
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Pyrazines / chemistry*
  • Pyrazines / pharmacology
  • Silver Compounds / chemical synthesis*
  • Silver Compounds / pharmacology*
  • X-Ray Diffraction

Substances

  • Anti-Bacterial Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Chelating Agents
  • Pyrazines
  • Silver Compounds
  • Diclofenac
  • 2,5-dimethylpyrazine