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Cyclisation of 7‐Deazaxanthine‐9‐propionic Acid to an Active‐Site‐Directed, Irreversibly Acting Inhibitor of Xanthine Oxidase
Author(s) -
Rosemeyer Helmut,
Kretschmer Uwe,
Seela Frank
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680811
Subject(s) - chemistry , alkylation , active site , stereochemistry , acylation , pyrimidine , ether cleavage , ether , xanthine oxidase , carbodiimide , medicinal chemistry , organic chemistry , enzyme , catalysis
Phase‐transfer alkylation of 2,4‐dimethoxy‐7 H ‐pyrrolo[2,3‐ d ]pyrimidine ( 2 ) with ethyl 3‐bromopropionate leads regioselectively to ethyl 2,3‐dimethoxy‐7 H ‐pyrrolo[2,3‐ d ]pyrimidine‐7‐propionate ( 3a ). After saponification and ether cleavage, the functionalised 7‐deazaxanthine 4b was obtained. Reaction of 4b with H 2 O‐soluble carbodiimide resulted in an intramolecular acylation at N(3) with formation of the tricyclic compound 5 . Compound 5 ‐ bearing a reactive lactam ring ‐ is an active‐site‐directed, irreversibly acting inhibitor of xanthine oxidase from cow's milk.