Synthesis and properties of a new water-soluble prodrug of the adenosine A 2A receptor antagonist MSX-2.
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.
Vollmann
Karl
K
Pharma-Center Bonn, Pharmaceutical Institute, Pharmaceutical Chemistry I, An der Immenburg 4, D-53121 Bonn, Germany.
Qurishi
Ramatullah
R
Hockemeyer
Jörg
J
Müller
Christa E
CE
D058917:Adenosine A2 Receptor Antagonists; D000818:Animals; D043182:Carboxylesterase / Q000378:metabolism; D019281:Dimerization; D004355:Drug Stability; D006863:Hydrogen-Ion Concentration / Q000187:drug effects; D006868:Hydrolysis / Q000187:drug effects; D011355:Prodrugs / Q000138:chemical synthesis* / Q000494:pharmacology*; D012995:Solubility / Q000187:drug effects; D013552:Swine; D014867:Water / Q000378:metabolism*; D014970:Xanthines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C113601:3-(3-hydroxypropyl)-8-(3-methoxystyryl)-7-methyl-1-propargylxanthine; D058917:Adenosine A2 Receptor Antagonists; D011355:Prodrugs; D014970:Xanthines; D014867:Water; D043182:Carboxylesterase