✦ LIBER ✦
Cyclisation of 7-Deazaxanthine-9-propionic Acid to an Active-Site-Directed, Irreversibly Acting Inhibitor of Xanthine Oxidase
✍ Scribed by Helmut Rosemeyer; Uwe Kretschmer; Frank Seela
- Publisher
- John Wiley and Sons
- Year
- 1985
- Tongue
- German
- Weight
- 470 KB
- Volume
- 68
- Category
- Article
- ISSN
- 0018-019X
No coin nor oath required. For personal study only.
✦ Synopsis
~ ~~
Phase-transfer alkylation of 2,4-dimethoxy-7H-pyrrolo[2,3-d]pyrimidine (2) with ethyl 3-bromopropionate leads regioselectively to ethyl 2,3-dimethoxy-7H-pyrrolo(2,3-d]pyrimidine-7-propionate (3a). After saponification and ether cleavage, the functionalised 7-deazaxanthine 4b was obtained. Reaction of 4b with H20-soluble carbodiimide resulted in an intramolecular acylation at N(3) with formation of the tricyclic compound 5. Compound 5bearing a reactive lactam ring ~ is an active-site-directed, irreversibly acting inhibitor of xanthine oxidase from cow's milk.
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