Synthesis and characterization in solid and solution of trans-dichloro-1-(2', 6'-difluorophenyl)-1H,3H-thiazolo [3,4-a]-benzimidazole(tri-n-propyl-phosphine)-palladium(II)": a palladium(II) complex of a ligand with anti-HIV properties

J Inorg Biochem. 1997 Feb 1;65(2):97-102. doi: 10.1016/s0162-0134(96)00093-1.

Abstract

The 1-(2',6'-difluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazole (L), a highly potent nonnucleoside HIV-1 reverse transcriptase inhibitor, has been reacted with [Pd2Cl4(PPr3n)2] in order to study its coordinating properties towards metal ions. The structure of the synthesized product has been examined in solution by 1H and 13C NMR, and in solid by X-ray analysis. [Pd(PPr3n)(L)Cl2] has a trans structure and L coordinates through imine nitrogen. The loss of anti-HIV properties of L, by complexation, suggests that, unless biological inactivation is simple due to steric reasons, the imine nitrogen atom is an active site of the molecule.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemical synthesis
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology*
  • Binding Sites
  • Crystallography, X-Ray
  • Drug Evaluation, Preclinical
  • HIV-1 / drug effects*
  • In Vitro Techniques
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology*
  • Palladium / chemistry
  • Palladium / pharmacology*
  • Solutions

Substances

  • Anti-HIV Agents
  • Ligands
  • Organometallic Compounds
  • Solutions
  • dichloro-1-(2',6'-difluorophenyl)-1H,3H-thiazolo(3,4-a)-benzimidazole(tri-n-propylphosphine)palladium(II)
  • Palladium