Making bispirin: synthesis, structure and activity against Helicobacter pylori of bismuth(III) acetylsalicylate

Chem Commun (Camb). 2013 Apr 11;49(28):2870-2. doi: 10.1039/c3cc40645h.

Abstract

Reaction of Bi(O(t)Bu)3 with aspirin (acetylsalicylic acid = aspH) in dry toluene results in the bismuth(III) complex, [Bi(O2C(C6H4)OAc)3]∞ 1 (O2C(C6H4)OAc = asp), minimum inhibitory concentration (MIC) against Helicobacter pylori ≥ 6.25 μg mL(-1), while the inclusion of a stoichiometric equivalent of KO(t)Bu leads to crystals of the bismuthate salt [KBi(O2C(C6H4)OAc)4]∞ 2.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Aspirin / analogs & derivatives*
  • Aspirin / chemical synthesis
  • Aspirin / chemistry*
  • Aspirin / pharmacology
  • Bismuth / chemistry*
  • Chemistry Techniques, Synthetic
  • Coordination Complexes / chemical synthesis*
  • Coordination Complexes / chemistry
  • Coordination Complexes / pharmacology*
  • Helicobacter pylori / drug effects*
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Coordination Complexes
  • Organometallic Compounds
  • bismuth(III) acetylsalicylate
  • Aspirin
  • Bismuth