Synthesis and properties of a new water-soluble prodrug of the adenosine A 2A receptor antagonist MSX-2

Molecules. 2008 Feb 12;13(2):348-59. doi: 10.3390/molecules13020348.

Abstract

The compound L-valine-3-{8-[(E)-2-[3-methoxyphenyl)ethenyl]-7-methyl-1-propargylxanthine-3-yl}propyl ester hydrochloride (MSX-4) was synthesized as an amino acid ester prodrug of the adenosine A2A receptor antagonist MSX-2. It was found to be stable in artificial gastric acid, but readily cleaved by pig liver esterase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine A2 Receptor Antagonists*
  • Animals
  • Carboxylesterase / metabolism
  • Dimerization
  • Drug Stability
  • Hydrogen-Ion Concentration / drug effects
  • Hydrolysis / drug effects
  • Prodrugs / chemical synthesis*
  • Prodrugs / pharmacology*
  • Solubility / drug effects
  • Swine
  • Water / metabolism*
  • Xanthines / chemical synthesis*
  • Xanthines / chemistry
  • Xanthines / pharmacology*

Substances

  • 3-(3-hydroxypropyl)-8-(3-methoxystyryl)-7-methyl-1-propargylxanthine
  • Adenosine A2 Receptor Antagonists
  • Prodrugs
  • Xanthines
  • Water
  • Carboxylesterase