ChemInform Abstract: 2-Nitro Analogues of Adenosine and 1-Deazaadenosine: Synthesis and Binding Studies at the Adenosine A1, A2A, and A3 Receptor Subtypes.
Abstract
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ChemInform Abstract
The effect of a nitro group at the 2-position in adenosine analogues (V) and (XIII) together with receptor selective N-6 substituents on the affinity at the adenosine title receptor is investigated. An efficient nitration reagent consists of a mixture of tetrabutylammonium nitrate and trifluoroacetic anhydride. Competing methanolysis of the nitro group of (III) is reduced to a minor process. For the preparation of parent compound (IX), a three-step procedure avoids the use of ammonia. The analogues (V) and (XIII) show good adenosine receptor activity, demonstrating directable selectivity for the A1, A2A, and A3 adenosine receptor subtypes.
