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Issue 2, 2014
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Design, synthesis and evaluation of N6-substituted 2-aminoadenosine-5′-N-methylcarboxamides as A3 adenosine receptor agonists

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Abstract

A series of N6-substituted 2-aminoadenosine-5′-N-methylcarboxamides were synthesized from the versatile intermediate, O6-(benzotriazol-1-yl)-2-amino-2′,3′-O-isopropylideneinosine-5′-N-methylcarboxamide (1). These compounds were evaluated as A3 adenosine receptor agonists in terms of their potency and receptor sub-type selectivity in a cAMP accumulation assay and a number of potent and selective compounds were identified. One such compound, 2-amino-N6-(3-chlorobenzyl)adenosine-5′-N-methylcarboxamide (3i), was over 500-fold selective for the A3AR over the other three adenosine receptor subtypes. This represents a significantly greater selectivity profile compared with the prototypical IB-MECA.

Graphical abstract: Design, synthesis and evaluation of N6-substituted 2-aminoadenosine-5′-N-methylcarboxamides as A3 adenosine receptor agonists

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Supplementary files

Article information


Submitted
29 Nov 2013
Accepted
18 Dec 2013
First published
20 Dec 2013

Med. Chem. Commun., 2014,5, 192-196
Article type
Concise Article
Author version available

Design, synthesis and evaluation of N6-substituted 2-aminoadenosine-5′-N-methylcarboxamides as A3 adenosine receptor agonists

S. M. Devine, L. T. May and P. J. Scammells, Med. Chem. Commun., 2014, 5, 192
DOI: 10.1039/C3MD00364G

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