synthesis, characterization and in vitro antiamoebic activity of 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones and their Palladium (II) and Ruthenium (II) complexes

Eur J Med Chem. 2004 May;39(5):459-65. doi: 10.1016/j.ejmech.2004.02.003.

Abstract

Synthesis of new Palladium(II) and Ruthenium(II) complexes of the type, [Pd(L)Cl(2)] and [Ru(eta(4)-C(8)H(12))(L)Cl(2)] [where, L = thiosemicarbazones derived from 5-nitrothiophene-2-carboxaldehyde and cycloalkylaminothiocarbonyl hydrazines] have been isolated by the reaction of [Pd(DMSO)(2)Cl(2)] and [Ru(eta(4)-C(8)H(12))(CH(3)CN)(2)Cl(2)] with 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones. The spectral data revealed that the thiosemicarbazones act as bidentate ligands, making use of thionic sulphur and the azomethine nitrogen atom for coordination to the central metal ion. Microdilution method was used for the assessment of antiamoebic activity of all the compounds against HK-9 strain of Entamoeba histolytica. Among all the thiosemicarbazones, 5-NT-4-BPTSCN (3) showed significant antiamoebic activity (IC(50) - 2.56 microM). Enhancement of antiamoebic activity resulted by introducing palladium and ruthenium metals in the thiosemicarbazone moiety. All the Pd(II) and Ru(II) complexes of 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones were found more active then their respective ligands. The complexes 1a-4a, 1b and 3b showed antiamoebic activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amebicides* / chemical synthesis
  • Amebicides* / chemistry
  • Amebicides* / pharmacology
  • Animals
  • Entamoeba histolytica / drug effects
  • Inhibitory Concentration 50
  • Molecular Structure
  • Organometallic Compounds* / chemical synthesis
  • Organometallic Compounds* / chemistry
  • Organometallic Compounds* / pharmacology
  • Palladium / chemistry*
  • Parasitic Sensitivity Tests
  • Ruthenium / chemistry*
  • Spectrum Analysis / methods
  • Thiosemicarbazones* / chemical synthesis
  • Thiosemicarbazones* / chemistry
  • Thiosemicarbazones* / pharmacology

Substances

  • Amebicides
  • Organometallic Compounds
  • Thiosemicarbazones
  • Palladium
  • Ruthenium