title: (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.
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.
authors.affiliation: University of Namur, 61 Rue de Bruxelles, B-5000 Namur, Belgium.
authors.forename: Raphaël
authors.initials: R
authors.lastname: Frédérick
authors.forename: Frederic
authors.initials: F
authors.lastname: Ooms
authors.forename: Neal
authors.initials: N
authors.lastname: Castagnoli
authors.forename: Jacques P
authors.initials: JP
authors.lastname: Petzer
authors.forename: Jiang-Fan
authors.initials: JF
authors.lastname: Feng
authors.forename: Michael A
authors.initials: MA
authors.lastname: Schwarzschild
authors.forename: Cornelis J
authors.initials: CJ
authors.lastname: Van der Schyf
authors.forename: Johan
authors.initials: J
authors.lastname: Wouters
mesh_terms: D058917:Adenosine A2 Receptor Antagonists; D008958:Models, Molecular; D008968:Molecular Conformation; D008996:Monoamine Oxidase Inhibitors / Q000494:pharmacology*; D055672:Static Electricity; D014970:Xanthines / Q000737:chemistry / Q000494:pharmacology*
chemical_list: C515416:8-(3-Chlorostyryl)-1,3,7-trimethylxanthine; D058917:Adenosine A2 Receptor Antagonists; D008996:Monoamine Oxidase Inhibitors; D014970:Xanthines