(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.
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.
Frédérick
Raphaël
R
University of Namur, 61 Rue de Bruxelles, B-5000 Namur, Belgium.
Ooms
Frederic
F
Castagnoli
Neal
N
Petzer
Jacques P
JP
Feng
Jiang-Fan
JF
Schwarzschild
Michael A
MA
Van der Schyf
Cornelis J
CJ
Wouters
Johan
J
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*
C515416:8-(3-Chlorostyryl)-1,3,7-trimethylxanthine; D058917:Adenosine A2 Receptor Antagonists; D008996:Monoamine Oxidase Inhibitors; D014970:Xanthines