2-Nitro analogues of adenosine and 1-deazaadenosine: synthesis and binding studies at the adenosine A1, A2A and A3 receptor subtypes

M J Wanner; J K Von Frijtag Drabbe Künzel; A P Ijzerman; G J Koomen

doi:10.1016/s0960-894x(00)00415-7

2-Nitro analogues of adenosine and 1-deazaadenosine: synthesis and binding studies at the adenosine A1, A2A and A3 receptor subtypes

Bioorg Med Chem Lett. 2000 Sep 18;10(18):2141-4. doi: 10.1016/s0960-894x(00)00415-7.

Authors

M J Wanner¹, J K Von Frijtag Drabbe Künzel, A P Ijzerman, G J Koomen

Affiliation

¹ Laboratory of Organic Chemistry, Institute of Molecular Chemistry, University of Amsterdam, The Netherlands.

PMID: 10999489
DOI: 10.1016/s0960-894x(00)00415-7

Abstract

The influence of nitro substituents on the properties of adenosine and 1-deazaadenosine was studied. Combination of a nitro group at the 2-position with several N6 substituents such as cyclopentyl and m-iodobenzyl gave a series of analogues with good adenosine receptor affinity, showing directable selectivity for the A1, A2A and A3 adenosine receptor subtypes.

Publication types

Comparative Study

MeSH terms

Adenosine / analogs & derivatives*
Adenosine / chemical synthesis
Adenosine / metabolism*
Animals
Binding Sites
Humans
Ligands
Protein Binding
Purinergic P1 Receptor Agonists
Radioligand Assay
Rats
Receptor, Adenosine A2A
Receptor, Adenosine A3
Receptors, Purinergic P1 / metabolism
Tubercidin / analogs & derivatives*
Tubercidin / chemical synthesis
Tubercidin / metabolism

Substances

Ligands
Purinergic P1 Receptor Agonists
Receptor, Adenosine A2A
Receptor, Adenosine A3
Receptors, Purinergic P1
Adenosine
Tubercidin