The synthesis of new adenosine A3 selective ligands containing bioisosteric isoxazoles

J P Mogensen; S M Roberts; A N Bowler; C Thomsen; L J Knutsen

doi:10.1016/s0960-894x(98)00302-3

The synthesis of new adenosine A3 selective ligands containing bioisosteric isoxazoles

Bioorg Med Chem Lett. 1998 Jul 7;8(13):1767-70. doi: 10.1016/s0960-894x(98)00302-3.

Authors

J P Mogensen¹, S M Roberts, A N Bowler, C Thomsen, L J Knutsen

Affiliation

¹ Novo Nordisk A/S, Måløv, Denmark.

PMID: 9873431
DOI: 10.1016/s0960-894x(98)00302-3

Abstract

The synthesis and purinergic receptor binding of novel adenosine A3 ligands is described. Many selective A3 receptor agonists e.g. N-(3-iodobenzyl)adenosine-5'-methyluronamide (IB-MECA) contain a 4'-ribosylalkylamide moiety. We found that this amide and other 4'-functional groups could be replaced with an isosteric isoxazole, and the target molecules retained potent binding to the recombinant human A3 receptor.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adenosine / analogs & derivatives*
Adenosine / chemistry
Adenosine / metabolism
Animals
Cell Line
Humans
Isoxazoles / chemistry*
Ligands
Rats
Receptors, Purinergic P1 / metabolism*
Recombinant Proteins / metabolism
Structure-Activity Relationship

Substances

Isoxazoles
Ligands
Receptors, Purinergic P1
Recombinant Proteins
N(6)-(3-iodobenzyl)-5'-N-methylcarboxamidoadenosine
Adenosine