Non-enzymatic reduction of a 1,2,4-thiadiazolium derivative

Bioorg Med Chem Lett. 2008 Mar 15;18(6):2172-8. doi: 10.1016/j.bmcl.2008.01.029. Epub 2008 Jan 11.

Abstract

It was discovered that 2,3-bis-(2-methoxy-phenyl)-5-phenylamino-[1,2,4]-thiadiazolium bromide (1), a 1,2,4-thiadiazolium derivative, could be reduced to the corresponding imidoylthiourea, 1-[(2-methoxy-phenyl)-(2-methoxy-phenylimino)-methyl]-3-phenyl-thiourea (3), by some biologically interesting reducing reagents including glutathione, cysteine, and ascorbic acid. The reduction also occurred in Sprague-Dawley rat and Yorkshire swine plasma, suggesting that thiol containing biological molecules existing in the plasma are mainly responsible for this reaction. A facile method for preparation of 3 from 1 was established by using 2-thioethanol as reaction reagent as well as solvent. The structure of 3 was fully characterized using nuclear magnetic resonance (NMR) and mass spectrometry with electrospray ionization source (ESI-MS). Those new findings could shed light on the development of 1,2,4-thiadiazolium derivatives for their potential pharmaceutical applications.

MeSH terms

  • Animals
  • Antioxidants / pharmacology*
  • Ascorbic Acid / pharmacology*
  • Chromatography, High Pressure Liquid
  • Cysteine / pharmacology*
  • Glutathione / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Rats
  • Rats, Sprague-Dawley
  • Spectrometry, Mass, Electrospray Ionization
  • Swine
  • Thiourea / analogs & derivatives*
  • Thiourea / chemistry
  • Thiourea / isolation & purification

Substances

  • 1-((2-methoxy-phenyl)-(2-methoxy-phenylimino)methyl)-3-phenyl-thiourea
  • Antioxidants
  • Glutathione
  • Thiourea
  • Cysteine
  • Ascorbic Acid