(E)-8-(3-Chlorostyryl)-1,3,7-trimethylxanthine, a caffeine derivative acting both as antagonist of adenosine A2A receptors and as inhibitor of MAO-B

Acta Crystallogr C. 2005 Sep;61(Pt 9):o531-2. doi: 10.1107/S0108270105023140. Epub 2005 Aug 10.

Abstract

In the crystal structure of (E)-8-(3-chlorostyryl)-1,3,7-trimethylxanthine (CSC) [systematic name: (E)-8-(3-chlorostyryl)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione], C16H15ClN4O2, the xanthine ring and the lateral styryl chain are coplanar. The crystal packing involves mainly parallel stacking of these planar molecules. The electrostatic potential calculated on the crystal structure conformation confirms the pharmacophore elements associated with MAO-B inhibition.

MeSH terms

  • Adenosine A2 Receptor Antagonists*
  • Models, Molecular
  • Molecular Conformation
  • Monoamine Oxidase Inhibitors / pharmacology*
  • Static Electricity
  • Xanthines / chemistry
  • Xanthines / pharmacology*

Substances

  • 8-(3-Chlorostyryl)-1,3,7-trimethylxanthine
  • Adenosine A2 Receptor Antagonists
  • Monoamine Oxidase Inhibitors
  • Xanthines