Issue 2, 2014

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

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

Supplementary files

Article information

Article type
Concise Article
Submitted
29 Nov 2013
Accepted
18 Dec 2013
First published
20 Dec 2013

Med. Chem. Commun., 2014,5, 192-196

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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