Efficient synthesis of an adenosine A2a agonist: glycosylation of 2-haloadenines and an N2-alkyl-6-chloroguanine |
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Authors: | Caddell John M Chapman Alan M Cooley Bob E Downey Brian P LeBlanc Michael P Jackson Mary M O'Connell Thomas M Phung Hahn-My Roper Thomas D Xie Shiping |
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Institution: | Chemical Development, GlaxoSmithKline, Research Triangle Park, North Carolina 27709, USA. |
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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. |
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