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J Org Chem
; 69(9): 3212-5, 2004 Apr 30.
Article
in English
| MEDLINE
| ID: mdl-15104468
ABSTRACT
A convergent synthesis of adenosine A2a agonist 1 in the form of its maleate salt 2 was achieved. The key step in this approach was the highly selective 9beta-glycosylation reaction between 2-haloadenines or an N(2)-alkyl-6-chloroguanine and a D-ribose derivative containing a 2-ethyltetrazolyl moiety. Glycosylations of other purine derivatives were also examined, and the methods developed provide efficient access to a variety of adenosine analogues such as 2-alkylaminoadenosines, an attractive class of compounds with antiinflammatory activity.
Subject(s)
Adenosine A2 Receptor Agonists , Adenosine/analogs & derivatives , Anti-Inflammatory Agents/chemical synthesis , Adenine/chemistry , Adenosine/chemical synthesis , Alkylation , Glycosylation , Guanine/analogs & derivatives , Hydrocarbons, Halogenated/chemistry , Maleates/chemistry , Molecular Structure , Purines/chemistry , Ribose/chemistry
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