Peer-Reviewed Journal Details
Mandatory Fields
Broadley, KJ;Burnell, E;Davies, RH;Lee, ATL;Snee, S;Thomas, EJ
2016
January
Organic & Biomolecular Chemistry
The synthesis of a series of adenosine A(3) receptor agonists
Published
WOS: 1 ()
Optional Fields
CERIUM(IV) AMMONIUM-NITRATE REGIOSELECTIVE SYNTHESIS ASYMMETRIC-SYNTHESIS METHYL CYANOFORMATE HIGH-YIELD AMINES PLATENSIMYCIN FACILE THIOSEMICARBAZONES CARBONYLATION
14
3765
3781
A series of 1'-(6-aminopurin-9-yl)-1'-deoxy-N-methyl-beta-D-ribofuranuronamides that were characterised by 2-diarkylamino-7-methyroxazolo[4,5-b]pyridin-5-ylmethyl substituents on N6 of interest for screening as selective adenosine A(3) receptor agonists, have been synthesised. This work involved the synthesis of 2-dialkylamino-5-aminomethyl-7-methyloxazolo[4,5-b]pyridines and analogues that were coupled with the known 1'-(6-chloropurin-9-yl)-1'-deoxy-N-methyl-p-o-ribofuranuronamide. The oxazolo[4,5-b]pyridines were synthesized by regioselective functionalisation of 2,4-dimethylpyridine N-oxides. The regioselectivities of these reactions were found to depend upon the nature of the heterocycle with 2-dimethylamino-5,7-dimethyloxazolo[4,5-b]pyridine-N-oxide undergoing regioselective functionalisation at the 7-methyl group on reaction with trifluoroacetic anhydride in contrast to the reaction of 4,6-dimethyl-3-hydroxypyridine-N-oxide with acetic anhydride that resulted in functionalisation of the 6-methyl group. To optimise selectivity for the A3 receptor, 5-aminomethyl-7-bromo-2-dimethylamino-4-[(3-methylisoxazol-5-yl)methoxylbenzo[cdoxazole was synthesised and coupled with the 1'-(6-chloropurin-9-0-r-deoxy-N-methyl-beta-D-ribofuranuronamide. The products were active as selective adenosine A3 agonists.
1477-0520
10.1039/c6ob00244g
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