Synthesis, characterization and biocidal activity of new organotin complexes of 2-(3-oxocyclohex-1-enyl)benzoic acid

Eur J Med Chem. 2010 Mar;45(3):883-9. doi: 10.1016/j.ejmech.2009.11.026. Epub 2009 Nov 18.

Abstract

The reaction of 1,3-cyclohexadione with 2-aminobenzoic acid has produced the 2-(3-oxocyclohex-1-enyl)benzoic acid (HOBz). Subsequent reactions of the ligand with organotin chlorides led to [Me(2)Sn(OBz)O](2) (1), [Bu(2)Sn(OBz)O](2) (2), [Ph(2)Sn(OBz)O](2) (3), [Me(3)Sn(OBz)] (4), [Bu(3)Sn(OBz)] (5) and [Ph(3)Sn(OBz)] (6). All complexes have been fully characterized. In addition the structure of complexes (2) and (4) have been authenticated by X-ray crystallography. The biological activity of all derivatives has been screened against Cryptococcus neoformans and Candida albicans. In addition we have performed toxicological testes employing human kidney cell. The complexes (3), (5) and (6) displayed the best values of inhibition of the fungus growing, superior to ketoconazole. Compound (5) presented promising results in view of the antifungal and cytotoxicity assays.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Benzoic Acid / chemistry*
  • Candida albicans / drug effects*
  • Cell Line
  • Cryptococcus neoformans / drug effects*
  • Crystallography, X-Ray
  • Cyclohexanecarboxylic Acids / chemistry*
  • Disinfectants / chemical synthesis*
  • Disinfectants / chemistry
  • Disinfectants / pharmacology*
  • Humans
  • Inhibitory Concentration 50
  • Models, Molecular
  • Molecular Structure
  • Organotin Compounds / chemical synthesis
  • Organotin Compounds / chemistry
  • Organotin Compounds / pharmacology

Substances

  • Antifungal Agents
  • Cyclohexanecarboxylic Acids
  • Disinfectants
  • Organotin Compounds
  • Benzoic Acid